Skip to main content

Furans and Benzofurans

  • Chapter
  • First Online:

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 29))

Abstract

This chapter reviews the significant developments in the metalation of furans and benzofurans and applications of the resulting metalated species in the past decade. New and interesting metalated furan and benzofuran derivatives and their novel reactions are featured. Topics encompass lithiation, magnesation and zincation, the use of boronated and other metalated furans and benzofurans in cross-coupling reactions, as well as the use of metalated furans and benzofurans in addition reactions. Examples of regioselective metalation are highlighted, and metalation of related furo heterocycles is also summarized.

This is a preview of subscription content, log in via an institution.

Buying options

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   299.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   379.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD   379.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

References

  1. Keay BA, Hopkins JM, Dibble PW (2008) Chapter 3.08: Furans and their benzo derivatives: applications. In: Katritzky AR, Ramsden CA, Scriven EFV, Taylor RJK (eds) Comprehensive heterocyclic chemistry III. Elsevier, Oxford

    Google Scholar 

  2. Aoyagi Y, Yamazaki A, Nakatsugawa C, Fukaya H, Takeya K, Kawauchi S, Izumi H (2008) Selvileucalin B, a novel diterpenoid with an unprecedented rearranged neoclerodane skeleton from Salvia ieucantha Cav. Org Lett 10:4429–4432

    Article  CAS  Google Scholar 

  3. Marion F, Williams DE, Patrick BO, Hollander I, Mallon R, Kim SC, Roll DM, Feldberg L, Van Soest R, Anderson RJ (2006) Liphagal, a selective inhibitor of PI3 kinase α isolated from the sponge Aka coralliphaga: structure elucidation and biomimetic synthesis. Org Lett 8:321–324

    Article  CAS  Google Scholar 

  4. Levin S, Nani RR, Reisman SE (2011) Enantioselective total synthesis of (+)-selvileucalin B. J Am Chem Soc 133:774–776

    Article  CAS  Google Scholar 

  5. Wright DL (2005) Chapter 1: Furans as versatile synthons for target-oriented and diversity-oriented synthesis. In: Gribble GW, Joule JA (eds) Progress in heterocyclic chemistry, vol 17. Elsevier, Oxford

    Google Scholar 

  6. Wong HNC, Yeung K-S, Yang Z (2008) Chapter 3.06: Furans and their benzo derivatives: reactivity. In: Katritzky AR, Ramsden CA, Scriven EFV, Taylor RJK (eds) Comprehensive heterocyclic chemistry III. Elsevier, Oxford

    Google Scholar 

  7. Yeung K-S, Yang Z, Peng X-S, Hou X-L (2010) Chapter 5.3: Five-membered ring systems: furans and benzofuran. In: Gribble GW, Joule JA (eds) Progress in heterocyclic chemistry, vol 22. Elsevier, Oxford

    Google Scholar 

  8. Lee HK, Wong HNC (2002) An enantioselective synthetic pathway towards plakortones. Chem Commun 2114–2115

    Google Scholar 

  9. Boukouvalas J, Loach RP (2008) General, regiodefined access to α-substituted butenolides through metal-halogen exchange of 3-bromo-2-silyloxyfurans. Efficient synthesis of an anti-inflammatory gorgonian lipid. J Org Chem 73:8109–8112

    Article  CAS  Google Scholar 

  10. Marcos IS, Hernández FA, Sexmero MJ, Basabe DDP, Pedrero AB, García N, Urones JG (2003) Synthesis and absolute configuration of (2)-chettaphanin I and (2)-chettaphanin II. Tetrahedron 59:685–694

    Article  CAS  Google Scholar 

  11. Chinchilla R, Nájera C, Yus M (2004) Metalated heterocycles and their applications in synthetic organic chemistry. Chem Rev 104:2667–2722

    Article  CAS  Google Scholar 

  12. Li JJ, Gribble GW (2000) Chapter 6: Furans and benzo[b]furans. In: Palladium in heterocyclic chemistry. A guide for the synthetic chemist. Pergamon, Oxford

    Google Scholar 

  13. Tofi M, Georgiou T, Montagnon T, Vassilikogiannakis G (2005) Regioselective ortho lithiation of 3-aryl and 3-styryl furans. Org Lett 7:3347–3350

    Article  CAS  Google Scholar 

  14. Stanetty P, Kolodziejczyk K, Roiban G-D, Mihovilovic MD (2006) Establishing the NHBoc functionality as ortho-metallating group for furan. Synlett 789–791

    Google Scholar 

  15. Sato N, Yue Q (2003) An efficient synthesis of cyanoarenes and cyanoheteroarenes via lithiation followed by electrophilic cyanation. Tetrahedron 59:5831–5836

    Article  CAS  Google Scholar 

  16. James CA, Coelho AL, Gevaert M, Forgione P, Snieckus V (2009) Combined directed ortho and remote metalation – Suzuki cross-coupling strategies. Efficient synthesis of heteroaryl-fused benzopyranones from biaryl O-carbamates. J Org Chem 74:4094–4103

    Article  CAS  Google Scholar 

  17. Kashulin IA, Nifant’ev IE (2004) Efficient method for the synthesis of hetarenoindanones based on 3-arylhetarenes and their conversion into hetarenoindenes. J Org Chem 69:5476–5479

    Article  CAS  Google Scholar 

  18. Tsubuki M, Okita H, Kaneko K, Shigihara A, Honda T (2009) Witting rearrangement of 3-furylmethyl ethers: facile synthesis of 3-methyl-2-furylmethanols and 3-furylmethanols. Heterocycles 77:433–444

    Article  CAS  Google Scholar 

  19. Devarie NO, Kim W-S, Smith AB III, Xian M (2009) Multicomponent type II anion relay chemistry (ARC): one-pot synthesis of 2,3-disubstituted furans and thiophenes. Org Lett 11:1861–1864

    Article  Google Scholar 

  20. Shanmugham MS, White JD (2004) A new route to furanoeremophilane sesquiterpenoids. Synthesis of (±)-6b-hydroxyeuryopsin. Chem Commun 44–45

    Google Scholar 

  21. Akai S, Kawashita N, Satoh H, Wada Y, Kakiguchi K, Kuriwaki I, Kita Y (2004) Highly regioselective nucleophilic carbon-carbon bond formation on furans and thiophenes initiated by Pummerer-type reaction. Org Lett 6:3793–3796

    Article  CAS  Google Scholar 

  22. Sanz R, Castroviejo MP, Fernández Y, Fañanás FJ (2005) A new and efficient synthesis of 4-functionalized benzo[b]furans from 2,3-dihalophenols. J Org Chem 70:6548–6551

    Article  CAS  Google Scholar 

  23. Mongin F, Bucher A, Bazureau JP, Bayh O, Awad H, Trecourt F (2005) Deprotonation of furans using lithium magnesates. Tetrahedron Lett 46:7989–7992

    Article  CAS  Google Scholar 

  24. Krasovsky A, Krasovskaya V, Knochel P (2006) Mixed Mg/Li amides of the type R2NMgCl·LiCl as highly efficient bases for the regioselective generation of functionalized aryl and heteroaryl magnesium compounds. Angew Chem Int Ed 45:2958–2961

    Article  Google Scholar 

  25. Melzig L, Rauhut CB, Knochel P (2009) 2,3-Functionalization of furans, benzofurans and thiophenes via magnesiation and sulfoxide–magnesium exchange. Chem Commun 3536–3538

    Google Scholar 

  26. Melzig L, Rauhut CB, Naredi-Rainer N, Knochel P (2011) Difunctionalisation of arenes and heteroarenes by directed metallation and sulfoxide–magnesium exchange. Chem Eur J 17:5362–5372

    Article  CAS  Google Scholar 

  27. X-j W, Sun X, Zhang L, Xu Y, Krihnamurthy D, Senanayake CH (2006) Noncryogenic I/Br-Mg exchange of aromatic halides bearing sensitive functional groups using i-PrMgCl-bis[2-(N,N-dimethylamino)ethyl]ether complexes. Org Lett 8:305–307

    Article  Google Scholar 

  28. Martin R, Buchwald SL (2007) Pd-catalyzed Kumada-Corriu cross-coupling reactions at low temperatures allow the use of Knochel-type Grignard reagents. J Am Chem Soc 129:3844–3845

    Article  CAS  Google Scholar 

  29. Haag BA, Samann C, Jana A, Knochel P (2011) Practical one-pot preparation of magnesium di(hetero)aryl- and magnesium dialkenylboronates for Suzuki–Miyaura cross-coupling reactions. Angew Chem Int Ed 50:7290–7294

    Article  CAS  Google Scholar 

  30. L’Helgoual’ch J-M, Seggio A, Chevallier F, Yonehara M, Jeanneau E, Uchiyama M, Mongin F (2008) Deprotonative metalation of five-membered aromatic heterocycles using mixed lithium-zinc species. J Org Chem 73:177–183

    Article  Google Scholar 

  31. Snégaroff K, Komagawa S, Chevallier F, Gros PC, Golhen S, Roisnel T, Uchiyama M, Mongin F (2010) Deprotonative metalation of substituted benzenes and heteroaromatics using amino/alkyl mixed lithium–zinc combinations. Chem Eur J 16:8191–8201

    Google Scholar 

  32. Wunderlich SH, Knochel P (2007) (tmp)2Zn⋅2MgCl2⋅2LiCl: a chemoselective base for the directed zincation of sensitive arenes and heteroarenes. Angew Chem Int Ed 46:7685–7688

    Article  CAS  Google Scholar 

  33. Snégaroff K, L’Helgoual’ch J-M, Bentabed-Ababsa G, Nguyen TT, Chevallier F, Yonehara M, Uchiyama M, Derdour A, Mongin F (2009) Deprotonative metalation of functionalized aromatics using mixed lithium–cadmium, lithium–indium, and lithium–zinc species. Chem Eur J 15:10280–10290

    Article  Google Scholar 

  34. Gauthier DR Jr, Szumigala RH Jr, Dormer PG, Armstron JD III, Volante RP, Reider PJ (2002) Synthesis of 5-pyridyl-2-furaldehydes via palladium-catalyzed cross-coupling with triorganozincates. Org Lett 4:375–378

    Article  CAS  Google Scholar 

  35. Rieke RD, Kim S-H (2011) 5-(1,3-Dioxolan-2-yl)-2-furanylzinc bromide; direct preparation, and its application for the synthesis of 5-substituted furan derivatives. Tetrahedron Lett 52:1128–1131

    Article  CAS  Google Scholar 

  36. Krasovskiy A, Malakhov V, Gavryushin A, Knochel P (2006) Efficient synthesis of functionalized organozinc compounds by the direct insertion of zinc into organic iodides and bromides. Angew Chem Int Ed 45:6040–6044

    Article  CAS  Google Scholar 

  37. Kim S-H, Rieke RD (2010) A convenient synthesis of 5-aryl- and 5-heteroaryl-2-furaldehydes by the cross-coupling reaction of organozincs. Tetrahedron Lett 51:2657–2659

    Article  CAS  Google Scholar 

  38. Valente C, Belowich ME, Hadei N, Organ MG (2010) Pd-PEPPSI complexes and the Negishi reaction. Eur J Org Chem 4343–4354

    Google Scholar 

  39. Organ MG, Calimsiz S, Sayah M, Hoi KH, Lough AJ (2009) Pd-PEPPSI-IPent: an active, sterically demanding cross-coupling catalyst and its application in the synthesis of tetra-ortho-substituted biaryls. Angew Chem Int Ed 48:2383–2387

    Article  CAS  Google Scholar 

  40. Sase S, Jaric M, Metzger A, Malakhov V, Knochel P (2008) One-pot Negishi cross-coupling reactions of in situ generated zinc reagents with aryl chlorides, bromides, and triflates. J Org Chem 73:7380–7382

    Article  CAS  Google Scholar 

  41. Huang Q, Rawal VH (2006) Total synthesis of (±)-bipinnatin J. Org Lett 8:543–545

    Article  CAS  Google Scholar 

  42. Xie L-G, Wang Z-X (2011) Nickel-catalyzed cross-coupling of aryltrimethylammonium iodides with organozinc reagents. Angew Chem Int Ed 50:4901–4904

    Article  CAS  Google Scholar 

  43. Molander GA, Canturk B, Kennedy LE (2009) Scope of the Suzuki-Miyaura cross-coupling reactions of potassium heteroaryltrifluoroborates. J Org Chem 74:973–980

    Article  CAS  Google Scholar 

  44. Dreher SD, Lim S-E, Sandrock DL, Molander GA (2009) Suzuki-Miyaura cross-coupling reactions of primary alkyltrifluoroborates with aryl chlorides. J Org Chem 74:3626–3631

    Article  CAS  Google Scholar 

  45. Molander GA, Gormisky PE, Sandrock DL (2008) Scope of aminomethylations via Suzuki-Miyaura cross-coupling of organotrifluoroborates. J Org Chem 73:2052–2057

    Article  CAS  Google Scholar 

  46. Molander GA, Jean-Gérard L (2009) Use of potassium β-trifluoroborato amides in Suzuki-Miyaura cross-coupling reactions. J Org Chem 74:5446–5450

    Article  CAS  Google Scholar 

  47. Knapp DM, Gillis EP, Burke MD (2009) A general solution for unstable boronic acids: slow-release cross-coupling from air-stable MIDA boronates. J Am Chem Soc 131:6961–6963

    Article  CAS  Google Scholar 

  48. Kinzel T, Zhang Y, Buchwald SL (2010) A new palladium precatalyst allows for the fast Suzuki-Miyaura coupling reactions of unstable polyfluorophenyl and 2-heteroaryl boronic acids. J Am Chem Soc 132:14073–14075

    Article  CAS  Google Scholar 

  49. Molander GA, Beaumard F (2010) Nickel-catalyzed C–O activation of phenol derivatives with potassium heteroaryltrifluoroborates. Org Lett 12:4022–4025

    Article  CAS  Google Scholar 

  50. Quasdorf KW, Antoft-Finch A, Liu P, Silberstein AL, Komaromi A, Blackburn T, Ramgren SD, Houk KN, Snieckus V, Garg NK (2011) Suzuki-Miyaura cross-coupling of aryl carbamates and sulfamates: experimental and computational studies. J Am Chem Soc 133:6352–6363

    Article  CAS  Google Scholar 

  51. Albaneze-Walker J, Raju R, Vance JA, Goodman AJ, Reeder MR, Liao J, Maust MT, Irish PA, Espino P, Andrews DR (2009) Imidazolylsulfonates: electrophilic partners in cross-coupling reactions. Org Lett 11:1463–1466

    Article  CAS  Google Scholar 

  52. Taylor RH, Felpin F-X (2007) Suzuki-Miyaura reactions of arenediazonium salts catalyzed by Pd(0)/C. One-pot chemoselective double cross-coupling reactions. Org Lett 9:2911–2914

    Article  CAS  Google Scholar 

  53. Bandgar BP, Bettigeri SV, Phopase J (2004) Unsymmetrical diaryl sulfones through palladium-catalyzed coupling of aryl boronic acids and arylsulfonyl chlorides. Org Lett 6:2105–2108

    Article  CAS  Google Scholar 

  54. Matsuda S, Takahashi M, Monguchi D, Mori A (2009) C–H and C–Si functionalization of furan derivatives: palladium-catalyzed homocoupling and arylation reactions. Synlett 1941–1944

    Google Scholar 

  55. Denmark SE, Baird JD, Regens CS (2008) Palladium-catalyzed cross-coupling of five-membered heterocyclic silanolates. J Org Chem 73:1440–1455

    Article  CAS  Google Scholar 

  56. Denmark SE, Smith RC, Chang W-TT, Muhuhi JM (2009) Cross-coupling reactions of aromatic and heteroaromatic silanolates with aromatic and heteroaromatic halides. J Am Chem Soc 131:3104–3118

    Article  CAS  Google Scholar 

  57. Cornella J, Lahlali H, Larrosa I (2010) Decarboxylative homocoupling of (hetero)aromatic carboxylic acids. Chem Commun 46:8276–8278

    Article  CAS  Google Scholar 

  58. Becht J-M, Catala C, Le Drian C, Wagner A (2007) Synthesis of biaryls via decarboxylative Pd-catalyzed cross-coupling reaction. Org Lett 9:1781–1783

    Article  CAS  Google Scholar 

  59. Goossen LJ, Rodriguez N, Linder C (2008) Decarboxylative biaryl synthesis from aromatic carboxylates and aryl triflates. J Am Chem Soc 130:15248–15249

    Article  CAS  Google Scholar 

  60. Goossen LJ, Rodriguez N, Linder C, Lange PP (2009) Biaryl and aryl ketone synthesis via Pd-catalyzed decarboxylative coupling of carboxylate salts with aryl triflates. Chem Eur J 15:9336–9349

    Article  CAS  Google Scholar 

  61. Forgione P, Brochu M-C, St-Onge M, Thesen KH, Bailey MD, Bilodeau F (2006) Unexpected intermolecular Pd-catalyzed cross-coupling reaction employing heteroaromatic carboxylic acids as coupling partners. J Am Chem Soc 128:11350–11351

    Article  CAS  Google Scholar 

  62. Zeni G, Alves D, Braga AL, Stefani HA, Nogueria CW (2004) Stereoselective sp2–sp2 bond formation via Negishi cross-coupling of vinylic tellurides and 2-heteroarylzinc chlorides. Tetrahedron Lett 45:4823–4826

    Article  CAS  Google Scholar 

  63. Zeni G, Lüdtke DS, Nogueria CW, Panatieri RB, Braga AL, Silveira CC, Stefani HA, Rocha JBT (2001) New acetylenic furan derivatives: synthesis and anti-inflammatory activity. Tetrahedron Lett 42:8927–8930

    Article  CAS  Google Scholar 

  64. Zeni G, Nogueria CW, Silva DO, Menezes PH, Braga AL, Stefani HA, Rocha JBT (2003) Palladium(II) chloride catalyzes the cross-coupling reaction of 2,5-bis-(butyltelluro)-furan and 1-alkynes. Tetrahedron Lett 44:1387–1390

    Article  CAS  Google Scholar 

  65. Cella R, Cunha RLOR, Reis AES, Pimenta DC, Klitzke CF, Stefani HA (2006) Suzuki-Miyaura cross-coupling reactions of aryl tellurides with potassium aryltrifluoroborate salts. J Org Chem 71:244–250

    Article  CAS  Google Scholar 

  66. Schröter S, Stock C, Bach T (2005) Regioselective cross-coupling reactions of multiple halogenated nitrogen-, oxygen-, and sulfur-containing heterocycles. Tetrahedron 61:2245–2267

    Article  Google Scholar 

  67. Burke MD, Berger EM, Schreiber SL (2004) A synthesis strategy yielding skeletally diverse small molecules combinatorially. J Am Chem Soc 126:14095–14104

    Article  CAS  Google Scholar 

  68. Tuan DT, Tung DT, Langer P (2006) Synthesis of 2-(2-arylethenyl)-5-arylfurans by regioselective palladium(0)-catalyzed coupling reactions of 2-(2-bromo-2-nitroethenyl)-5-bromofuran. Synlett 2812–2814

    Google Scholar 

  69. Hung NT, Hussain M, Malik I, Villinger A, Langer P (2010) Site-selective Suzuki cross-coupling reactions of 2,3-dibromobenzofuran. Tetrahedron Lett 51:2420–2422

    Article  Google Scholar 

  70. Morice C, Garrido F, Mann A, Suffert J (2002) Palladium assisted substitution of 3-benzo[b]furan triflates. Synlett 501–503

    Google Scholar 

  71. Masters K-S, Flynn BL (2010) An efficient synthesis of (±)-frondosin B using a Stille–Heck reaction sequence. Org Biomol Chem 8:1290–1292

    Article  CAS  Google Scholar 

  72. Lin S-Y, Chen C-L, Lee Y-J (2003) Total synthesis of ailanthoidol and precursor XH14 by Stille coupling. J Org Chem 68:2968–2971

    Article  CAS  Google Scholar 

  73. Bach T, Bartels M (2001) 2,3-Disubstituted and 2,3,5-trisubstituted benzofurans by regioselective Pd-catalyzed cross-coupling reactions; a short synthesis of eupomatenoid-15. Synlett 1284–1286

    Google Scholar 

  74. Bach T, Bartels M (2002) Synthesis of eupomatenoids by three consecutive transition metal-catalyzed cross-coupling reactions. Tetrahedron Lett 43:9125–9127

    Article  CAS  Google Scholar 

  75. Bach T, Bartels M (2003) Regioselective C–C bond formation reactions on 2,3-dibromo- and 2,3,5-tribromobenzofuran as an access to multiply substituted benzofurans. Total syntheses of eupomatenoids 3, 4, 5, 6, and 15. Synthesis 925–939

    Google Scholar 

  76. Luo Y-C, Zhang H-H, Liu Y-Z, Cheng R-L, Xu P-F (2009) An asymmetric approach to 5-O-carbamoyl-2-epi-polyoxamic acid and the total synthesis of 2″-epi-polyoxin J. Tetrahedron Asymmetry 20:1174–1180

    Article  CAS  Google Scholar 

  77. Enders D, Del Signore G (2004) Efficient asymmetric synthesis of a-(heteroaryl)alkylamines by 1,2-addition of lithiated hetarenes to aldehyde-SAMP-hydrazones. Tetrahedron Asymmetry 15:747–751

    Article  CAS  Google Scholar 

  78. Yamashita M, Yamada K-i, Tomioka K (2004) Construction of arene-fused-piperidine motifs by asymmetric addition of 2-trityloxymethylaryllithiums to nitroalkenes: the asymmetric synthesis of a dopamine D1 full agonist, A-86929. J Am Chem Soc 126:1954–1955

    Article  CAS  Google Scholar 

  79. Guinchard X, Denis J-N (2008) Reactions of in situ generated N-Boc nitrones with aromatic and heteroaromatic Grignard reagents: application to the synthesis of zileuton. J Org Chem 73:2028–2031

    Article  CAS  Google Scholar 

  80. Zhou S, Chen C-R, Gau H-M (2010) Highly enantioselective 3-furylation of ketones using (3-furyl)titanium nucleophile. Org Lett 12:48–51

    Article  CAS  Google Scholar 

  81. Wu K-H, Chuang D-W, Chen C-A, Gau H-M (2008) Chiral tertiary 2-furyl alcohols: diversified key intermediates to bioactive compounds. Their enantioselective synthesis via (2-furyl)aluminium addition to ketones catalyzed by a titanium catalyst of (S)-BINOL. Chem Commun 2343–2345

    Google Scholar 

  82. Sibi MP, He L (2004) Application of enantioselective radical reactions: synthesis of (+)-ricciocarpins a and b. Org Lett 6:1749–1752

    Article  CAS  Google Scholar 

  83. Furstner A, Weintritt H (1998) Total synthesis of roseophilin. J Am Chem Soc 120:2817–2825

    Article  Google Scholar 

  84. Lee S, MacMillan DWC (2007) Organocatalytic vinyl and Friedel-Crafts alkylations with trifluoroborate salts. J Am Chem Soc 129:15438–15439

    Article  CAS  Google Scholar 

  85. Reiter M, Torssell S, Lee S, MacMillan DWC (2010) The organocatalytic three-step total synthesis of (+)-frondosin B. Chem Sci 1:37–42

    Article  CAS  Google Scholar 

  86. Chan LY, Kim S, Chung WT, Long C, Kim S (2011) Fe(OTf)3-catalyzed reaction of benzylic acetates with organosilicon compounds. Synlett 415–419

    Google Scholar 

  87. Molander GA, Cavalcanti LN (2011) Metal-free chlorodeboronation of organotrifluoroborates. J Org Chem 76:7195–7203

    Article  CAS  Google Scholar 

  88. Abbiati G, Arcadi A, Marinelli F, Rossi E, Verdecchia M (2006) Rh-catalyzed sequential hydroarylation/hydrovinylation–heterocyclization of β-(2-aminophenyl)-α,β-ynones with organoboron derivatives: a new approach to functionalized quinolines. Synlett 3218–3224

    Google Scholar 

  89. Pommier A, Stepanenko V, Jarowicki K, Kocienski PJ (2003) Synthesis of (+)-manoalide via a copper(I)-mediated 1,2-metalate rearrangement. J Org Chem 68:4008–4013

    Article  CAS  Google Scholar 

  90. Chartoire A, Comoy C, Fort Y (2008) Furo[3,2-b]pyridine: a convenient unit for the synthesis of polyheterocycles. Tetrahedron 64:10867–10873

    Article  CAS  Google Scholar 

  91. Chartoire A, Comoy C, Fort Y (2010) Toolbox for regioselective lithiations of furo[2,3-c]pyridine. J Org Chem 75:2227–2235

    Article  CAS  Google Scholar 

  92. Henssier JT, Matzgar AJ (2009) Facile and scalable synthesis of the fused-ring heterocycles thieno[3,2-b]-thiophene and thieno[3,2-b]furan. Org Lett 11:3144–3147

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Kap-Sun Yeung .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2012 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Yeung, KS. (2012). Furans and Benzofurans. In: Gribble, G. (eds) Metalation of Azoles and Related Five-Membered Ring Heterocycles. Topics in Heterocyclic Chemistry, vol 29. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2012_79

Download citation

Publish with us

Policies and ethics