Abstract
Applications of five-membered ring products as catalysts in cyclometalation reactions include chiral reactions, metathesis reactions, cross-coupling reactions, and polymerization reactions. Other reactions include reductions, Michael addition reactions, dehydrogenations, Diels–Alder reactions, and hydrogenations.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Omae I (2004) Coord Chem Rev 248:995
Omae I (2007) J Organomet Chem 692:2608
Wild SB (1997) Coord Chem Rev 166:291
Albert J, Granell J, Muller G (2006) J Organomet Chem 691:2101
Djukic J-P (2008) Cyclopalladated compounds as resolving agents for racemic mixtures. In: Dupont J, Pfeffer M (eds) Palladacycles. Synthesis, characterization and applications. Wiley-VCH, Weinheim, p 123
Spencer J (2008) Other uses of palladacycles in synthesis. In: Dupont J, Pfeffer M (eds) Palladacycles. Synthesis, characterization and applications. Wiley-VCH, Weinheim, p 227
Fischer DF, Barakat A, Xin Z, Weiss MW, Peters R (2009) Chem Eur J 15:8722
Dunina VV (2011) Cur Org Chem 15:3415
Dunina VV, Gorunova ON, Zykov PA, Kochetkov KA (2011) Russ Chem Rev 80:51
Nishiyama H, Ito J (2010) Chem Commun 46:203
Djukic J-P, Hijazi A, Flack HD, Bernardinelli G (2008) Chem Soc Rev 37:406
Nishiyama H (2007) Chem Soc Rev 36:1133
Yu J-Q, Giri R, Chen X (2006) Org Biomol Chem 4:4041
Severin K, Bergs R, Beck W (1998) Angew Chem Int Ed 37:1634
Ohshima T, Kawabata T, Takeuchi Y, Kakinuma T, Iwasaki T, Yonezawa T, Murakimi H, Nishiyama H, Mashima K (2011) Angew Chem Int Ed 50:6296
Hollis TK, Overman LE (1999) J Organomet Chem 576:290
Overman LE, Owen CE, Pavan MM, Richards CJ (2003) Org Lett 5:1809
Anderson CE, Overman LE (2003) J Am Chem Soc 125:12412
Prasad RS, Anderson CE, Richards CJ, Overman LE (2005) Organometallics 24:77
Wu Y, Huo S, Gong J, Cui X, Ding L, Ding K, Du C, Liu Y, Song M (2001) J Organomet Chem 637–639:27
Wu YJ, Cui XL, Du CX, Wang WL, Guo RY, Chen RF (1998) J Chem Soc Dalton Trans 3727
Cui XL, Wu YJ, Yang LR (1999) Chin Chem Lett 10:127
Leung P-H, He G, Lang H, Liu A, Loh S-K, Selvaratnam S, Mok KF, White AJP, Williams DJ (2000) Tetrahedron 56:7
Yeo W-C, Vittal JJ, White AJP, Williams DJ, Leung P-H (2001) Organometallics 20:2167
Qin Y, White AJP, Williams DJ, Leung P-H (2002) Organometallics 21:171
Motoyama Y, Nishiyama H (2003) Yuki Gosei Kagaku Kyokaishi 61:343
Motoyama Y, Koga Y, Nishiyama H (2001) Tetrahedron 57:853
van der Boom ME, Milstein D (2003) Chem Rev 103:1759
Motoyama Y, Shimozono K, Aoki K, Nishiyama H (2002) Organometallics 21:1684
Singleton JT (2003) Tetrahedron 59:1837
Denmark SE, Stavenger RA, Faucher A-M, Edwards JP (1997) J Org Chem 62:3375
Motoyama Y, Okano M, Narusawa H, Makihara N, Aoki K, Nishiyama H (2001) Organometallics 20:1580
Cohen R, Milstein D, Martin JML (2004) Organometallics 23:2336
Albrecht M, van Koten G (2001) Angew Chem Int Ed 40:3750
Canty AJ, Denney MC, van Koten G, Skelton BW, White AH (2004) Organometallics 23:5432
Motoyama Y, Koga Y, Kobayashi K, Aoki K, Nishiyama H (2002) Chem Eur J 8:2968
Stark MA, Richards CJ (1997) Tetrahedron Lett 38:5881
Stark MA, Jones G, Richards CJ (2000) Organometallics 19:1282
Fossey JS, Richards CJ (2004) Organometallics 23:367
Hosokawa S, Ito J, Nishiyama H (2010) Organometallics 29:5773
Ito J, Ujiie S, Nishiyama H (2009) Organometallics 28:630
Ito J, Teshima T, Nishiyama H (2012) Chem Commun 48:1105
Matsumura K, Arai N, Hori K, Saito T, Sayo N, Ohkuma T (2011) J Am Chem Soc 133:10696
Cheow YL, Pullarkat SA, Li Y, Leung P-H (2012) J Organomet Chem 696:4215
Tran DN, Cramer N (2011) Angew Chem Chem Ed 50:11098
Weiss M, Frey W, Peters R (2012) Organometallics 31:6365
Samoiłowicz C, Bieniek M, Grela K (2009) Chem Rev 109:3708
Chauvin Y (2006) Angew Chem Chem Ed 45:3740
Grubbs RH (2006) Angew Chem Chem Ed 45:3760
Schrock RR (2006) Angew Chem Chem Ed 45:3748
Garber SB, Kingsbury JS, Gray BL, Hoveyda AH (2000) J Am Chem Soc 122:8168
Yao Q, Zhang Y (2003) Angew Chem Int Ed 42:3395
Yao Q, Sheets M (2005) J Organomet Chem 690:3577
Clavier H, Audic N, Guillemin J-C, Mauduit M (2005) J Organomet Chem 690:3585
Roye F, Vilain C, ElkaĂŻm L, Grimaud L (2003) Org Lett 5:2007
Harrity JPA, La DS, Cefalo DR, Visser MS, Hoveyda AH (1998) J Am Chem Soc 120:2343
Kingsbury JS, Harrity JPA, Bonitatebus PJ Jr, Hoveyda AH (1999) J Am Chem Soc 121:791
Mori M (2005) Yuki Gosei Kagaku Kyokaishi 63:423
Fukuyama T, Ryu T (2005) Yuki Gosei Kagaku Kyokaishi 63:503
Pietraszuk C, Fischer H, Rogalski S, Marciniec B (2005) J Organomet Chem 690:5912
Michaelis S, Blechert S (2005) Org Lett 7:5513
Mix S, Blechert S (2005) Org Lett 7:2015
Vehlow K, Maechling S, Blechert S (2006) Organometallics 25:25
Gillingham DG, Kataoka O, Garber SB, Hoveyda AH (2004) J Am Chem Soc 126:12288
BouzBouz S, Simmons R, Cossy J (2004) Org Lett 6:3465
Advanced Information on the Nobel Prize in Chemistry 2005, 30 November 2005
Tabari DS, Tolentino DR, Schrodi Y (2013) Organometallics 32:5
Trillo B, GulĂas M, LĂłpez F, Castedo L, Mascareñas JL (2005) J Organomet Chem 690:5609
Arisawa M, Terada Y, Theeraladanon C, Takahashi K, Nakagawa M, Nishida A (2005) J Organomet Chem 690:5398
Grela K, Harutyunyan S, Michrowska A (2002) Angew Chem Int Ed 41:4038
Rouhi AM (2003) Chem Eng News 23:34
Volugioukalakis GC, Grubbs RH (2010) Chem Rev 110:1746
Miki K, Inoue T, Ohe K (2013) Yuki Gosei Kagaku Kyokaishi 71:601
Schrodi Y, Pederson RL (2007) Adv Synth Catal 249:1
Grubbs RH (2004) Tetrahedron 60:7117
Grubbs RH (ed) (2003) Handbook of metathesis, vol 1–3. Wiley-VCH, Weinheim
Hryniewicka A, Kozłowska A, Witkowski S (2012) J Organomet Chem 701:87
HĂ©risson J-I, Chauvin Y (1971) Macromol Chem 141:161
Stewart IC, Ung T, Pletnev AA, Berlin JM, Gruffs RH, Schrodi Y (2007) Org Lett 9:1589
Murelli RP, Snapper ML (2007) Org Lett 9:1749
Ritter T, Hejl A, Wenzel AG, Funk TW, Grubbs RH (2006) Organometallics 25:5740
Benitez D, Goddard WA III (2005) J Am Chem Soc 127:12218
Haibach MC, Kundu S, Brookhart M, Goldman AS (2012) Acc Chem Res 45:947
ÄŚusak A (2012) Chem Eur J 18:5800
Vougioukalakis GC (2012) Chem Eur J 18:8868
Kress S, Blechert S (2012) Chem Soc Rev 41:4389
Peeck LH, Leuthäusser S, Plenio H (2010) Organometallics 29:4339
Fustero S, Bello P, MirĂł J, SimĂłn A, del Pozo C (2012) Chem Eur J 18:10991
Herbert MB, Lan Y, Keitz BK, Liu P, Endo K, Day MW, Houk KN, Grubbs RH (2012) J Am Chem Soc 134:7861
Khan RKM, O’Brien RV, Torker S, Li B, Hoveyda AH (2012) J Am Chem Soc 134:12774
Endo K, Grubbs RH (2011) J Am Chem Soc 133:8525
Vieille-Petit L, Clavier H, Linden A, Blumentritt S, Nolan SP, Dorta R (2010) Organometallics 29:775
Bieniek M, Samojłowicz C, Sashuk V, Bujok R, Śledź P, Lugan N, Lavigne G, Arlt D, Grela K (2011) Organometallics 30:4144
Savka RD, Plenio H (2012) J Organomet Chem 710:68
Jimenez LR, Gallon BJ, Schrodi Y (2010) Organometallics 29:3471
Mayer C, Gillingham DG, Ward TR, Hilvert D (2011) Chem Commun 47:12068
Żukowska K, Szadkowska A, Pazio AE, Woźniak K, Grela K (2012) Organometallics 31:462
Barbasiewicz M, Grudzień K, Malinska M (2012) Organometallics 31:3171
Peeck LH, Savka RD, Plenio H (2012) Chem Eur J 18:12845
Ohshima K (2005) Kagaku 65:12
Kagaku’s editors (2005) Kagaku 65:18
Su Y, Jiao N (2011) Curr Org Chem 15:3362
Alonso DA, Nájera C (2010) Chem Soc Rev 39:2891
Zapf A, Beller M (2005) Chem Commun 431
Beletskaya IP, Cheprakov AV (2004) J Organomet Chem 689:4055
Bedford RB (2003) Chem Commun 1787
Littke AF, Fu GC (2002) Angew Chem Int Ed 41:4176
Herrman WA, Böhm VPW, Reisenger C-P (1999) J Organomet Chem 576:23
Mori A (2004) Yuki Gosei Kagaku Kyokaishi 62:355
Nájera C, Alonso DA (2008) Application of cyclopalladated compounds as catalysts for Heck and Sonogashira reactions. In: Dupont J, Pfeffer M (eds) Palladacycles. Synthesis, characterization and applications. Wiley-VCH, Weinheim, p 155
Bedford RB (2008) Palladacyclic Pre-catalysts for Suzuki coupling, Buchwald-Hartwig amination and related reactions. In: Dupont J, Pfeffer M (eds) Palladacycles. Synthesis, characterization and applications. Wiley-VCH, Weinheim, p 209
Chinchilla R, Nájera C (2011) Chem Soc Rev 40:5084
Fihri A, Bouhrara M, Nekoueishahraki B, Basset J-M, Polshettiwar V (2011) Chem Soc Rev 40:5181
Sun C-L, Li B-J, Shi Z-J (2010) Chem Commun 46:677
Herrmann WA, Böhm VPW, Reisinger C-P (1999) J Organomet Chem 576:23
Herrmann WA, Brossmer C, Reisinger C-P, Riermeier TH, Ă–fele K, Beller M (1997) Chem Eur J 3:1357
Frey GD, Reisinger C-P, Herdtweck E, Hermann WA (2005) J Organomet Chem 690:3193
Frey GD, SchĂĽtz J, Herdweck E, Herrmann WA (2005) Organometallics 24:4416
Botella L, Nájera C (2002) J Organomet Chem 663:46
Albisson DA, Bedford RB, Lawrence SE, Scully PN (1998) Chem Commun 2095
Liang L-C, Chien P-S, Huanf M-H (2005) Organometallics 24:353
Juliá-Hernández F, Arcas A, Vincente J (2012) Chem Eur J 18:7780
Tsubomura T, Chiba M, Nagai S, Ishihira M, Matsumoto K, Tsukuda T (2011) J Organomet Chem 696:3657
Kozlov VA, Aleksanvan DV, Nelyubina YV, Lyssenko KA, Petrovskii PV, Vasil'ev AA, Odinets IL (2011) Organometallics 30:2920
Serrano JL, GarcĂa L, PĂ©rez J, PĂ©rez E, GarcĂa J, Sánchez G, Sehnal P, Ornellas SD, Williams TJ, Fairlamb IJS (2011) Organometallics 30:5095
CĂvicos JF, Gholinejad M, Alonso DA, Nájera C (2011) Chem Lett 40:907
Yu A, Li X, Peng D, Wu Y, Chang J (2012) Appl Organomet Chem 26:301
BĹ‚aszczyk I, Gniewek A, Trzeciak AM (2011) J Organomet Chem 696:3601
Huang M, Feng Y, Wu Y (2012) Tetrahedron 68:376
Zhang J, Medley CM, Krause JA, Guan H (2010) Organometallics 29:6393
Xu G, Li X, Sun H (2011) J Organomet Chem 696:3011
BĹ‚aszczyk I, Gniewek A, Trzeciak AM (2012) J Organomet Chem 710:44
Hajipour AR, Karami K, Rafiee F (2012) Appl Organomet Chem 26:27
Hajipour AR, Rafiee F (2012) Appl Organomet Chem 26:51
Awano T, Ohmura T, Suginome M (2011) J Am Chem Soc 133:20738
Huang X, Anderson KW, Zim D, Jiang L, Klapars A, Buchwald SL (2003) J Am Chem Soc 125:6653
Tobisu M, Xu T, Shimasaki T, Chatani N (2011) J Am Chem Soc 133:19505
Lyons TW, Hull KL, Sanford MS (2011) J Am Chem Soc 133:4455
Pérez MA, Quijada R, Ortega-Jiménez F, Alvarez-Toledano C (2005) J Mol Catal A Chem 226:291
McGowan KP, Veige AS (2012) J Organomet Chem 711:10
Thagfi JA, Lavoie GG (2012) Organometallics 31:2463
Frazier KA, Froese RD, He Y, Klosin J, Theriault CN, Vosejpka PC, Zhou Z, Abboud KA (2011) Organometallics 30:3318
Liu Z, Gao W, Liu X, Luo X, Cui D, Mu Y (2011) Organometallics 30:752
Luconi L, Rossin A, Tuci G, Tritto I, Boggioni L, Klosin JJ, Theriault CN, Giambastiani G (2012) Chem Eur J 18:671
Martinez-Arripe E, Jean-Baptiste-dit-Dominique F, Auffrant A, Goff X-FL, Thuilliez J, Nief F (2012) Organometallics 31:4854
Mungwe N, Swarts AJ, Mapolie SF, Westman G (2011) J Organomet Chem 696:3527
Liu Z, Gao W, Zhang J, Cui D, Wu Q, Mu Y (2010) Organometallics 29:5783
Wang L, Cui D, Hou Z, Li W, Li Y (2011) Organometallics 30:760
Zeng H, Guan Z (2011) J Am Chem Soc 133:1159
Khlebnikov V, Meduri A, Mueller-Bunz H, Montini T, Fornasiero P, Zangrando E, Milani B, Albrecht M (2012) Organometallics 31:976
Jensen CM (1999) Chem Commun 2443
Renkema KB, Kissin YV, Goldman AS (2003) J Am Chem Soc 125:7770
Zhang X, Fried A, Knapp S, Goldman AS (2003) Chem Commun 2060
Dobereiner GE, Crabtree RH (2010) Chem Rev 110:681
Gnanamgari D, Sauer ELO, Schley ND, Butler C, Incarvito CD, Crabtree RH (2009) Organometallics 28:321
Gu X-Q, Chen W, Morales-Morales D, Jensen CM (2002) J Mol Catal A Chem 189:119
Bernskoetter WH, Brookhart M (2008) Organometallics 27:2036
Du W, Wang L, Wu P, Yu Z (2012) Chem Eur J 18:11550
Gruver BC, Adams JJ, Warner SJ, Arulsamy N, Roddick DM (2011) Organometallics 30:5133
Punji B, Emge TJ, Goldman AS (2010) Organometallics 29:2702
Adams JJ, Arulsamy N, Roddick DM (2012) Organometallics 31:1439
Ogata K, Sasano D, Yokoi T, Isozaki K, Seike H, Yasuda N, Ogawa T, Kurata H, Takaya H, Nakamura M (2012) Chem Lett 41:194
Ogata K, Sasano D, Yokoi T, Isozaki K, Seike H, Takaya H, Nakamura M (2012) Chem Lett 41:498
Shiota A, Malinakova HC (2012) J Organomet Chem 704:9
Liu T-P, Liao Y-X, Xing C-H, Hu Q-S (2011) Org Lett 13:2452
Bhattacharya P, Krause JA, Guan H (2011) Organometallics 30:4720
Chakraborty S, Krause JA, Guan H (2009) Organometallics 28:582
Author information
Authors and Affiliations
Rights and permissions
Copyright information
© 2014 Springer Japan
About this chapter
Cite this chapter
Omae, I. (2014). Applications of Five-Membered Ring Products as Catalysts in Cyclometalation Reactions. In: Cyclometalation Reactions. Springer, Tokyo. https://doi.org/10.1007/978-4-431-54604-7_8
Download citation
DOI: https://doi.org/10.1007/978-4-431-54604-7_8
Published:
Publisher Name: Springer, Tokyo
Print ISBN: 978-4-431-54603-0
Online ISBN: 978-4-431-54604-7
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)