Directed Metallation pp 85-116 | Cite as
Chelate-Directed Oxidative Functionalization of Carbon–Hydrogen Bonds: Synthetic Applications and Mechanistic Insights
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Abstract
This chapter describes advances over the past four decades in Pd-mediated and Pd-catalyzed reactions for the highly regioselective oxidative functionalization of C–H bonds. The synthetic utility and the key mechanistic features of both stoichiometric and catalytic C–X (X = O, Cl, Br, I, F, N) bond-forming reactions are presented. The intermediacy of high oxidation state PdIV species in many of these transformations has allowed for bond constructions that were not previously possible through traditional Pd0/PdII couples.
C–H bond cleavage Chelation Carbon–heteroatom Palladium Palladium(IV)
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References
- 1.Cope AC, Siekman RW (1965) J Am Chem Soc 87:3272 CrossRefGoogle Scholar
- 2.Ryabov AD (1985) Synthesis 233 Google Scholar
- 3.Newkome GR, Puckett WE, Gupta VK, Kiefer GE (1986) Chem Rev 86:451 CrossRefGoogle Scholar
- 4.Dunina VV, Zalevskaya OA, Potapov VM (1988) Russ Chem Rev 57:434 CrossRefGoogle Scholar
- 5.Constable AG, McDonald WS, Sawkins LC, Shaw BL (1978) J Chem Soc Chem Commun 1061 Google Scholar
- 6.Constable AG, McDonald WS, Sawkins LC, Shaw BL (1980) J Chem Soc Dalton Trans 1992 Google Scholar
- 7.Baldwin JE, Jones RH, Najera C, Yus M (1985) Tetrahedron 41:699 CrossRefGoogle Scholar
- 8.Baldwin JE, Nájera C, Yus M (1985) J Chem Soc Chem Commun 126 Google Scholar
- 9.Mahapatra AK, Bandyopadhyay D, Bandyopadhyay P, Chakravorty A (1986) Inorg Chem 25:2214 CrossRefGoogle Scholar
- 10.Sinha C, Bandyopadhyay D, Chakravorty A (1988) Inorg Chem 27:1173 CrossRefGoogle Scholar
- 11.Pal CK, Chattopadhyay S, Sinha C, Chakravorty A (1992) J Organomet Chem 439:91 CrossRefGoogle Scholar
- 12.Sinha CR, Bandyopadhyay D, Chakravorty A (1988) J Chem Soc Chem Commun 468 Google Scholar
- 13.Bhaumik R, Bandyopadhyay P (1996) Transition Met Chem 21:187 CrossRefGoogle Scholar
- 14.Alsters PL, Teunissen HT, Boersma J, van Koten G (1990) Recl Trav Chim Pays Bas 109:487 Google Scholar
- 15.Alsters PL, Teunissen HT, Boersma J, Spek AL, van Koten G (1993) Organometallics 12:4691 CrossRefGoogle Scholar
- 16.Valk J, Boersma J, van Koten G (1996) Organometallics 15:4366 CrossRefGoogle Scholar
- 17.Mahapatra AK, Bandyopadhyay D, Bandyopadhyay P, Chakravorty A (1984) J Chem Soc Chem Commun 999 Google Scholar
- 18.Kamaraj K, Bandyapadhyay D (1997) J Am Chem Soc 119:8099 CrossRefGoogle Scholar
- 19.Kamaraj K, Bandyapadhyay D (1999) Organometallics 18:438 CrossRefGoogle Scholar
- 20.Wadhwani P, Bandyapadhyay D (2000) Organometallics 19:4435 CrossRefGoogle Scholar
- 21.Bhaumik R, Biswas H, Bandyopadhyay P (1995) J Organomet Chem 498:81 CrossRefGoogle Scholar
- 22.Alsters PL, Boersma J, van Koten G (1991) Tetrahedron Lett 32:675 CrossRefGoogle Scholar
- 23.Alsters PL, Boersma J, van Koten G (1993) Organometallics 12:1629 CrossRefGoogle Scholar
- 24.Bäckvall J (1975) Tetrahedron Lett 16:2225 CrossRefGoogle Scholar
- 25.Bäckvall J, Björkman EE (1980) J Org Chem 45:2893 CrossRefGoogle Scholar
- 26.Carr K, Sutherland JK (1984) J Chem Soc Chem Commun 1227 Google Scholar
- 27.Carr K, Saxton HM, Sutherland JK (1988) J Chem Soc Perkin Trans 1599 Google Scholar
- 28.Bore L, Honda T, Gribble GW (2000) J Org Chem 65:6278 CrossRefGoogle Scholar
- 29.Justicia J, Oltra JE, Cuerva JM (2004) Tetrahedron Lett 45:4293 CrossRefGoogle Scholar
- 30.Justicia J, Oltra JE, Cuerva JM (2005) J Org Chem 70:8265 CrossRefGoogle Scholar
- 31.Dick AR, Kampf JW, Sanford MS (2005) J Am Chem Soc 127:12790 CrossRefGoogle Scholar
- 32.Alsters PL, Engel PF, Hogerheide MP, Copijn M, Spek AL, van Koten G (1993) Organometallics 12:1831 CrossRefGoogle Scholar
- 33.Lagunas M, Gossage RA, Spek AL, van Koten G (1998) Organometallics 17:731 CrossRefGoogle Scholar
- 34.Vicente J, Saura-Llamas I, Bautista D (2005) Organometallics 24:6001 CrossRefGoogle Scholar
- 35.Bartolomé C, Espinet P, Martín-Álvarez JM, Villafañe F (2003) Inorg Chim Acta 347:49 CrossRefGoogle Scholar
- 36.Dick AR, Remy MS, Kampf JW, Sanford MS (2007) Organometallics 26:1365 CrossRefGoogle Scholar
- 37.Yu J, Giri R, Chen X (2006) Org Biomol Chem 4:4041 CrossRefGoogle Scholar
- 38.Dick AR, Sanford MS (2006) Tetrahedron 62:2439 CrossRefGoogle Scholar
- 39.Kalyani D, Deprez NR, Desai LV, Sanford MS (2005) J Am Chem Soc 127:7330 CrossRefGoogle Scholar
- 40.Henry PM (1971) J Org Chem 36:1886 CrossRefGoogle Scholar
- 41.Stock LM, Tse K, Vorvick LJ, Walstrum SA (1981) J Org Chem 46:1757 CrossRefGoogle Scholar
- 42.Eberson L, Jonson L (1974) J Chem Soc Chem Commun 885 Google Scholar
- 43.Eberson L, Jonson L (1976) Acta Chem Scand B 30:361 CrossRefGoogle Scholar
- 44.Eberson L, Jonson L (1977) Liebigs Ann Chem 233 Google Scholar
- 45.Yoneyama T, Crabtree RH (1996) J Mol Catal A 108:35 CrossRefGoogle Scholar
- 46.Dick AR, Hull KL, Sanford MS (2004) J Am Chem Soc 126:2300 CrossRefGoogle Scholar
- 47.Kalyani D, Sanford MS (2005) Org Lett 7:4149 CrossRefGoogle Scholar
- 48.Dick AR, Kampf JW, Sanford MS (2005) Organometallics 24:482 CrossRefGoogle Scholar
- 49.Schardt BC, Hill CL (1983) Inorg Chem 22:1563 CrossRefGoogle Scholar
- 50.Desai LV, Hull KL, Sanford MS (2004) J Am Chem Soc 126:9542 CrossRefGoogle Scholar
- 51.Dangel BD, Johnson JA, Sames D (2001) J Am Chem Soc 123:8149 CrossRefGoogle Scholar
- 52.Green TW, Wuts PGM (1999) Protective groups in organic synthesis. Wiley, New York CrossRefGoogle Scholar
- 53.Umino N, Iwakuma T, Ikezaki M, Itoh N (1978) Chem Pharm Bull 26:2897 Google Scholar
- 54.Kalberer EW, Whitfield SR, Sanford MS (2006) J Mol Catal A 251:108 CrossRefGoogle Scholar
- 55.Wang D, Hao X, Wu D, Yu J (2006) Org Lett 8:3387 CrossRefGoogle Scholar
- 56.Desai LV, Malik HA, Sanford MS (2006) Org Lett 8:1141 CrossRefGoogle Scholar
- 57.Reddy BVS, Reddy LR, Corey EJ (2006) Org Lett 8:3391 CrossRefGoogle Scholar
- 58.Giri R, Liang J, Lei J, Li J, Wang D, Chen X, Naggar IC, Guo C, Foxman BM, Yu J (2005) Angew Chem Int Ed 44:7420 CrossRefGoogle Scholar
- 59.Fahey DR (1970) Chem Commun 417 Google Scholar
- 60.Fahey DR (1971) J Organomet Chem 27:283 CrossRefGoogle Scholar
- 61.Chen X, Hao X, Goodhue CE, Yu J (2006) J Am Chem Soc 128:6790 CrossRefGoogle Scholar
- 62.Roy AH, Hartwig JF (2004) Organometallics 23:1533 CrossRefGoogle Scholar
- 63.Kodama H, Katsuhira T, Nishida T, Hino T, Tsubata K (2001) Chem Abstr 135:344284 Google Scholar
- 64.Kalyani D, Dick AR, Anani WQ, Sanford MS (2006) Org Lett 8:2523 CrossRefGoogle Scholar
- 65.Kalyani D, Dick AR, Anani WQ, Sanford MS (2006) Tetrahedron 62:11483 CrossRefGoogle Scholar
- 66.Wan X, Ma Z, Li B, Zhang K, Cao S, Zhang S, Shi Z (2006) J Am Chem Soc 128:7416 CrossRefGoogle Scholar
- 67.Giri R, Chen X, Yu J (2005) Angew Chem Int Ed 44:2112 CrossRefGoogle Scholar
- 68.Giri R, Chen X, Hao X, Li J, Liang J, Fan Z, Yu J (2005) Tetrahedron Asymmetry 16:3502 CrossRefGoogle Scholar
- 69.Giri R, Wasa M, Breazzano SP, Yu J (2006) Org Lett 8:5685 CrossRefGoogle Scholar
- 70.Ibrahim H, Togni A (2004) Chem Commun 1147 Google Scholar
- 71.Hamashima Y, Suzuki T, Takano H, Shimura Y, Sodeoka M (2005) J Am Chem Soc 127:10164 CrossRefGoogle Scholar
- 72.Hull KL, Anani WQ, Sanford MS (2006) J Am Chem Soc 128:7134 CrossRefGoogle Scholar
- 73.Grushin VV (2002) Chem Eur J 8:1006 CrossRefGoogle Scholar
- 74.Tsang WCP, Zheng N, Buchwald SL (2005) J Am Chem Soc 127:14560 CrossRefGoogle Scholar
- 75.Uemura T, Imoto S, Chatani N (2006) Chem Lett 35:842 CrossRefGoogle Scholar
- 76.Hartwig JF (2002) Handbook of organopalladium chemistry for organic synthesis. Wiley-Interscience, New York Google Scholar
- 77.Yang BH, Buchwald SL (1999) J Organomet Chem 576:125 CrossRefGoogle Scholar
- 78.Thu H, Yu W, Che C (2006) J Am Chem Soc 128:9048 CrossRefGoogle Scholar
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