Abstract
There are two applications for cyclometalation reactions and five-membered ring products for synthetic purposes. The first is synthesis of five-membered ring products by cyclometalation reactions. The second is synthesis of the derivatives of five-membered ring products or their intermediates during cyclometalation reactions. Pincer products are also used for synthesis of their derivatives.
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Omae I (1972) Rev Silicon Germanium Tin Lead Comp 1:59
Omae I (1979) Chem Rev 79:287
Omae I (1979) Coord Chem Rev 28:97
Omae I (1979) Kagaku No Ryoiki 33:767
Omae I (1980) Coord Chem Rev 32:235
Omae I (1982) Coord Chem Rev 42:31
Omae I (1982) Angew Chem Int Ed 21:889; (1982) Angew Chem 94:902
Omae I (1982) Yuki Gosei Kagaku Kyokaishi 40:147
Omae I (1982) Coord Chem Rev 42:245
Omae I (1982) Kagaku Kogyo 33:989
Omae I (1983) Coord Chem Rev 51:1
Omae I (1984) Coord Chem Rev 53:261
Omae I (1988) Coord Chem Rev 83:137
Omae I (1998) Kagaku Kogyo 49:303
Omae I, Aoki A, Horiguchi K (1998) Kagaku Kogyo 49:469
Omae I (2004) Coord Chem Rev 248:995
Omae I (2004) Phosphorus Sulfur Silicon 179:891
Omae I (2007) J Organomet Chem 692:2608
Omae I (2010) Appl Organometal Chem 24:347
Omae I (2011) J Organomet Chem 696:1128
Omae I (1986) Organometallic intramolecular-coordination compounds, J Organomet Chem Library 18. Elsevier, Amsterdam
Omae I (1989) Organotin chemistry, J Organomet Chem Library 21. Elsevier, Amsterdam
Omae I (1998) Applications of organometallic compounds. Wiley, NewYork
Jun C-H, Lee H, Hong J-B (1997) J Org Chem 62:1200
Lee D-Y, Moon CW, Jun C-H (2002) J Org Chem 67:3945
Chang D-H, Lee D-Y, Hong B-S, Choi J-H, Jun C-H (2004) J Am Chem Soc 126:424
Kim D-W, Lim S-G, Jun C-H (2006) Org Lett 8:2937
Park J-W, Park J-H, Jun C-H (2008) J Org Chem 73:5598
Padilla R, Salazar V, Paneque M, Alvarado-Rodríguez JG, Tamariz J, Pacheco-Cuvas H, Vattier F (2010) Organometallics 29:2835
Basolo F, Johnson R (1964) Coordination chemistry. The Benjamin/Cummings Publishing Company, London
Zucca A, Cordeschi D, Stoccoro S, Cinellu MA, Minghetti G, Chelucci G, Manassero M (2011) Organometallics 30:3064
Zhao S-B, Wang R-Y, Wang S (2007) J Am Chem Soc 129:3092
Crosby SH, Clarkson GJ, Rourke JP (2009) J Am Chem Soc 131:14142
Crosby SH, Clarkson GJ, Deeth RJ, Rourke JP (2010) Organometallics 29:1966
Crosby SH, Clarkson GJ, Rourke JP (2011) Organometallics 30:3603
Thomas HR, Deeth RJ, Clarkson GJ, Rourke JP (2011) Organometallics 30:5641
Canty AJ, Honeyman RT (1990) J Organomet Chem 387:247
Maidich L, Zuri G, Stoccoro S, Cinellu MA, Masia M, Zucca A (2013) Organometallics 32:438
Petretto GL, Rourke JP, Maidich L, Stoccoro S, Cinellu MA, Minghetti G, Clarkson GJ, Zucca A (2012) Organometallics 31:2971
Zucca A, Doppiu A, Cinellu MA, Stoccoro S, Minghetti G, Manassero M (2002) Organometallics 21:783
Minghetti G, Stoccoro S, Cinellu MA, Soro B, Zucca A (2003) Organometallics 22:4770
Zucca A, Petretto GL, Stoccoro S, Cinellu MA, Minghetti G, Manassero M, Manassero C, Male L, Albinati A (2006) Organometallics 25:2253
Minghetti G, Stoccoro S, Cinellu MA, Petretto L, Zucca A (2008) Organometallics 27:3415
Butschke B, Schröder D, Schwarz H (2009) Organometallics 28:4340
Butschke B, Schwarz H (2010) Organometallics 29:6002
Butschke B, Schlangen M, Schröder D, Schwarz H (2008) Chem Eur J 14:11050
Butschke B, Tabrizi SG, Schwarz H (2010) Chem Eur J 16:3962
Zucca A, Petretto GL, Stoccoro S, Cinellu MA, Manassero M, Manassero C, Minghetti G (2009) Organometallics 28:2150
Britovsek GJP, Taylor RA, Sunley GJ, Law DJ, White AJP (2006) Organometallics 25:2074
Zucca A, Cinellu MA, Pinna MV, Stoccoro S, Minghetti G (2000) Organometallics 19:4295
Shibata T, Takayasu S, Yuzawa S, Otani T (2012) Org Lett 14:5106
Kwak J, Ohk Y, Jung Y, Chang S (2012) J Am Chem Soc 134:17778
Young KJH, Yousufuddin M, Ess DH, Periana RA (2009) Organometallics 28:3395
Young KJH, Mironov OA, Periana RA (2007) Organometallics 26:2137
Tyo EC, Castleman AW Jr, Schröderk D, Milko P, Roithova J, Ortega JM, Cinellu MA, Cocco F, Minghetti G (2009) J Am Chem Soc 131:13009
Cocco F, Cinellu MA, Minghetti G, Zucca A, Stoccoro S, Maiore L, Manassero M (2010) Organometallics 29:1064
Zhao J-W, Wang C-M, Zhang J, Zheng S-T, Yang G-Y (2008) Chem Eur J 14:9223
Cartoon MEK, Cheeseman GWH (1982) J Organomet Chem 234:123
Dupont J, Pfeffer M (1987) J Organomet Chem 321:C13
Robinson NP, Depree GJ, de Wit RW, Main L, Nicholson BK (2005) J Organomet Chem 690:3827
Takahashi H, Tsuji J (1967) J Organomet Chem 10:511
Thompson JM, Heck RF (1975) J Org Chem 40:2667
Carbayo A, Cuevas JV, García-Herbosa G (2002) J Organomet Chem 658:15
Murahashi S, Horiie S (1956) J Am Chem Soc 78:4816
Horiie S (1958) Nippon Kagaku Zasshi 79:499
Horiie S (1960) Chem Abstr 54:4607
Horiie S, Murahashi S (1960) Bull Chem Soc Jpn 33:88
Sokolov VI, Troitskaya LL, Reutov OA (1979) J Organomet Chem 182:537
Ryabov AD, Firsova YN, Goral VN, Ryabova ES, Shevelkova AN, Troitskaya LL, Demeschik TV, Sokolov VI (1998) Chem Eur J 4:806
Yamamoto Y, Yamazaki H (1980) Inorg Chim Acta 41:229
Yamamoto Y, Yamazaki H (1976) Synthesis 750
Holton RA (1977) Tetrahedron Lett 355
Brisdon BJ, Nair P, Dyke SF (1981) Tetrahedron 37:173
Julia M, Duteil M, Lallemand JY (1975) J Organomet Chem 102:239
Kamiyama S, Kimura T, Kasahara A, Izumi T, Maemura M (1979) Bull Chem Soc Jpn 52:142
Ryabov AD (1985) Synthesis 233
Barr N, Dyke SF, Quessy SN (1983) J Organomet Chem 253:391
Girling IR, Widdowson DA (1982) Tetrahedron Lett 23:1957
Bahsoun A, Dehand J, Pfeffer M, Zinsius M (1979) J Chem Soc Dalton Trans 547
Dehand J, Mutet C, Pfeffer M (1981) J Organomet Chem 209:255
Mutet C, Pfeffer M (1979) J Organomet Chem 171:C34
Maassarani F, Pfeffer M, Borgne GL (1987) Organometallics 6:2029
Beydoun N, Pfeffer M, Cian AD, Fischer J (1991) Organometallics 10:3693
Pfeffer M (1992) Pure Appl Chem 64:335; Beydoun N, Pfeffer M (1990) Synthesis 729; Ossorf H, Pfeffer M, Jastrzebski JTBH, Stam CH (1987) Inorg Chem 26:1169
Pfeffer P, Rotteveel MA, Sutter J-P, Cian AD, Fischer J (1989) J Organomet Chem 371:C21
Depree GJ, Main L, Nicholson BK, Robinson NP, Jameson GB (2006) J Organomet Chem 691:667
Holton RA, Natalie KJ Jr (1981) Tetrahedron Lett 22:267
Clark PW, Dyke HJ, Dyke SF, Perry G (1983) J Organomet Chem 253:399
Troitskaya LL, Khrushcheva NS, Sokolov VL, Reutov OA (1982) Zh Org Khim 18:2606; (1983) Chem Abstr 98:126327d
Heck RF (1968) J Am Chem Soc 90:313
Murahashi S (1955) J Am Chem Soc 77:6403
Horiie S, Murahashi S (1960) Bull Chem Soc Jpn 33:247
Kleiman JP, Dubeck M (1963) J Am Chem Soc 85:1544
Cravotto G, Demartin F, Palmisano G, Penoni A, Radice T, Tollari S (2005) J Organomet Chem 690:2017
Stock LM, Brown HC (1963) Adv Phys Org Chem 1:35
Allison JAC, El Khadem HS, Wilson CAJ (1975) Heterocyclic Chem 12:1275
Sokolov VI, Troitskaya LL, Khrushchova NS (1983) J Organomet Chem 250:439
Klein H-F, Helwig M, Koch U, Flörke U, Haupt H-J (1993) Z Naturforsch 48b:778
Morimoto T, Chatani N, Murai S (1999) J Am Chem Soc 121:1758
Murai S (1994) J Synth Org Chem Jpn 52:992
Borman S (1993) Chem Eng News 6, Dec 13
Murai S, Kakiuchi F, Sekine S, Tanaka Y, Kamatani A, Sonoda M, Chatani N (1993) Nature 366:529
Murai S, Kakiuchi F, Sekine S, Tanaka Y, Kamatani A, Sonoda M, Chatani N (1994) Pure Appl Chem 66:1527
Kakiuchi F, Sekine S, Tanaka Y, Kamatani A, Sonoda M, Chatani N, Murai S (1995) Bull Chem Soc Jpn 68:62
Fujii N, Kakiuchi F, Chatani N, Murai S (1996) Chem Lett 939
Fujii N, Kakiuchi F, Yamada A, Chatani N, Murai S (1997) Chem Lett 425
Fujii N, Kakiuchi F, Yamada A, Chatani N, Murai S (1998) Bull Chem Soc Jpn 71:285
Kakiuchi F, Gendre PL, Yamada A, Ohtaki H, Murai S (2000) Tetrahedron Asymmetry 11:2647
Kakiuchi F, Tsujimoto T, Sonoda M, Chatani N, Murai S (2001) Synlett 948
Kakiuchi F, Murai S (2002) Acc Chem Res 35:826
Kakiuchi F, Matsumoto M, Tsuchiya K, Igi K, Hayamizu T, Chatani N, Murai S (2003) J Organomet Chem 686:134
Willis MC, McNally SJ, Beswick PJ (2004) Angew Chem Int Ed 43:340
Tanaka M, Imai M, Yamamoto Y, Tanaka K, Shimowatari M, Nagumo S, Kawahara N, Suemune H (2003) Org Lett 5:1365
Bendorf HD, Colella CM, Dixon EC, Marchetti M, Matukonis AN, Musselman JD, Tiley TA (2002) Tetrahedron Lett 43:7031
Jordan RF, Taylor DF (1989) J Am Chem Soc 111:778
Chang K-J, Rayabarapu DK, Cheng C-H (2003) Org Lett 5:3963
Chang K-J, Rayabarapu DK, Cheng C-H (2004) J Org Chem 69:4781
Chatani N, Ie Y, Kakiuchi F, Murai S (1999) J Am Chem Soc 121:8645
Knowles WS (1983) Acc Chem Res 16:106
Halpern J (1982) Acc Chem Res 15:332
Chinkov N, Sklute G, Chechik H, Abramovitch A, Amsallem D, Varghese J, Majumdar S, Marek I (2004) Pure Appl Chem 76:517
Dremt E, Budzelaar PHM (1996) Chem Rev 96:663
Sen A (1986) Adv Polym Sci 73(74):125
Sen A (1993) Acc Chem Res 26:303
Ash CE (1994) J Mater Educ 16:1
Liu J, Heaton BT, Iggo JA, Whyman R (2004) Angew Chem Int Ed 43:90
Murakami M, Tsuruta T, Ito Y (2000) Angew Chem Int Ed 39:2484
Kim M, Liu Q, Gabbaï FP (2004) Organometallics 23:5560
Matsuda T (2006) Yuki Gosei Kagaku Kyokaishi 64:780
Herrmann WA, Böhm VPW, Reisinger C-P (1999) J Organomet Chem 576:23
Albrecht M (2010) Chem Rev 110:576
Balcells D, Clot E, Eisenstein O (2010) Chem Rev 110:749
Kuhl N, Hopkinson MN, Wencel-Delord J, Glorius F (2012) Angew Chem Int Ed 51:10236
Niu J-L, Hao X-Q, Gong J-F, Song M-P (2011) Dalton Trans 40:5135
Lyons TW, Sanford MS (2010) Chem Rev 110:1147
Neufeldt SR, Sanford MS (2012) Acc Chem Res 45:936
Engle KM, Mei T-S, Wasa M, Yu J-Q (2012) Acc Chem Res 45:788
Song W, Ackermann L (2012) Angew Chem Int Ed 51:8251
Li H, Wei W, Xu Y, Zhang C, Wan X (2011) Chem Commun 47:1497
Lyons TW, Hull KL, Sanford MS (2011) J Am Chem Soc 133:4455
Kalyani D, Deprez NR, Desai LV, Sanford MS (2005) J Am Chem Soc 127:7330
Baudoin O (2011) Chem Soc Rev 40:4902
Guo H-M, Jiang L-L, Niu H-Y, Rao W-H, Liang L, Mao R-Z, Li D-Y, Qu G-R (2011) Org Lett 13:2008
Lakshman MK, Deb AC, Chamala RR, Pradhan P, Protap R (2011) Angew Chem Int Ed 50:11400
Cornella J, Righi M, Lassosa I (2011) Angew Chem Int Ed 50:9429
Ackermann L, Vicente R, Potukuchi HK, Pirovano V (2010) Org Lett 12:5032
Karthikeyan J, Cheng C-H (2011) Angew Chem Int Ed 50:9880
Rakshit S, Grohamann C, Besset T, Glorius F (2011) J Am Chem Soc 133:2350
Park SH, Kim JY, Chang S (2011) Org Lett 13:2372
Hashimoto Y, Ueyama T, Fukutani T, Hirano K, Satoh T, Miura M (2011) Chem Lett 40:1165
Schröder N, Besset T, Glorius F (2012) Adv Synth Catal 354:579
Wang C, Chen H, Wang Z, Chen J, Huang Y (2012) Angew Chem Int Ed 51:7242
Li X, Gong X, Zhao M, Song G, Deng J, Li X (2011) Org Lett 13:5808
Wang F, Song G, Li X (2010) Org Lett 12:5430
Zhu C, Falck JR (2011) Org Lett 13:1214
Ackermann L, Pospech J (2011) Org Lett 13:4153
Guimond N, Gouliaras C, Fagnou K (2010) J Am Chem Soc 132:6908
Ackermann L, Fenner S (2011) Org Lett 13:6548
Ackermann L, Lygin AV, Hofmann N (2011) Angew Chem Int Ed 50:6379
Su Y, Zhao M, Han K, Song G, Li X (2010) Org Lett 12:5462
Too PC, Wang Y-F, Chiba S (2010) Org Lett 12:5688
Yoshida Y, Kurahashi T, Matsubara S (2011) Chem Lett 40:1140
Kuninobu Y, Takai K (2012) Bull Chem Soc Jpn 85:656
Patureau FW, Besset T, Kuhl N, Glorius F (2011) J Am Chem Soc 133:2154
Aguilar D, Bielsa R, Soler T, Urriolabeitia EP (2011) Organometallics 30:642
Chen Q, IIies L, Nakamura E (2011) J Am Chem Soc 133:428
Zhao Y, Chen G (2011) Org Lett 13:4850
IIies L, Chen Q, Zeng X, Nakamura E (2011) J Am Chem Soc 133:5221
Xiao F, Shuai Q, Zhao F, Baslé O, Deng G, Li C-J (2011) Org Lett 13:1614
Shen Z-L, Goh KKK, Cheong H-L, Wong CHA, Lai Y-C, Yang Y-S, Loh T-P (2010) J Am Chem Soc 132:15852
Sharma S, Park E, Park J, Kim IS (2012) Org Lett 14:906
Xie R, Fu H, Ling Y (2011) Chem Commun 47:8976
Xu W, Jin Y, Liu H, Jiang Y, Fu H (2011) Org Lett 13:1274
Yoo EJ, Ma S, Mei T-S, Chan KSL, Yu J-Q (2011) J Am Chem Soc 133:7652
Xu S, Lu J, Fu H (2011) Chem Commun 47:5596
Ryu J, Shin K, Park SH, Kim JY, Chang S (2012) Angew Chem Int Ed 51:9904
Schröder N, Wencel-Delord J, Glorius F (2012) J Am Chem Soc 134:8298
Chan KSL, Wasa M, Wang X, Yu J-Q (2011) Angew Chem Int Ed 50:9081
Niu L, Yang H, Yang D, Fu H (2012) Adv Synth Catal 354:2211
Sakurai T, Matsuoka Y, Hanataka T, Fukuyama N, Namikoshi T, Watanabe S, Murata M (2012) Chem Lett 41:374
Simmons EM, Hartwig JF (2010) J Am Chem Soc 132:17092
Du Y, Hyster TK, Rovis T (2011) Chem Commun 47:12074
Kim J, Chang S (2010) J Am Chem Soc 132:10272
Li L, Yu P, Cheng J, Chen F, Pan C (2012) Chem Lett 41:600
Wang W, Pan C, Chen F, Cheng J (2011) Chem Commun 47:3978
Ackermann L, Kozhushkov SI, Yufit DS (2012) Chem Eur J 18:12068
Tsai AS, Tauchert ME, Bergman RG, Ellman JA (2011) J Am Chem Soc 133:1248
Li Y, Zhang X-S, Chen K, He K-H, Pan F, Li B-J, Shi Z-J (2012) Org Lett 14:636
Peng X, Zhu Y, Ramirez TA, Zhao B, Shi Y (2011) Org Lett 13:5244
Kitahara M, Umeda N, Hirano K, Satoh T, Miura M (2011) J Am Chem Soc 133:2160
Enthaler S, Company A (2011) Chem Soc Rev 40:4912
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Omae, I. (2014). Applications of Cyclometalation Reactions and Five-Membered Ring Products for Synthetic Purposes. In: Cyclometalation Reactions. Springer, Tokyo. https://doi.org/10.1007/978-4-431-54604-7_7
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