Pd-catalyzed cyclodimerization of alkenyl and aryl dibromides: Construction of dibenzo[a,e]cyclooctatetraenes

doi:10.1016/S1872-2067(14)60201-1

Abstract

Abstract:

Cyclooctatetraenes, including dibenzocyclooctatetraenes, are structurally interesting compounds and are widely used in many areas. Therefore, the development of synthetic methods for such compounds has long been attractive. In this work, a Pd-catalyzed coupling reaction between alkenylbromides and arylbromides has been realized. Multi-substituted 1,4-dibromo-1,3-butadienes and o-bromo-2-(2-bromovinyl)benzenes underwent a Pd-catalyzed cyclodimerization reaction to afford the corresponding multi-substituted cyclooctatetraenes and dibenzo[a,e] cyclooctatetraenes, respectively, in high yields and with excellent regioselectivity.

Key words: Dibromide, Cyclooctatetraene, Dibenzo[a,e]cyclooctatetraene, 1,4-Dibromo-1,3-butadiene, Homo-coupling, Palladium catalyst

Kunbing Ouyang, Zhenfeng Xi. Pd-catalyzed cyclodimerization of alkenyl and aryl dibromides: Construction of dibenzo[a,e]cyclooctatetraenes[J]. Chinese Journal of Catalysis, 2015, 36(1): 24-32.

×
share this article

Add to citation manager EndNote|Ris|BibTeX

URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(14)60201-1

https://www.cjcatal.com/EN/Y2015/V36/I1/24

References

[1] Huisgen R, Mietzsch F. Angew Chem Int Ed, 1964, 3: 83
[2] Paquette L A. Tetrahedron, 1975, 31: 2855
[3] Schumann H. Angew Chem Int Ed, 1984, 23: 474
[4] Paquette L A. Acc Chem Res, 1993, 26: 57
[5] Klärner F G. Angew Chem Int Ed, 2001, 40: 3977
[6] Nishinaga T, Ohmae T, Iyoda M. Symmetry, 2010, 2: 76
[7] Edelmann F T. Angew Chem Int Ed, 1995, 34: 2466
[8] Edelmann F T. New J Chem, 1995, 19: 535
[9] Edelmann F T. In: Abel E W, Stone F G A, Wilkinson G eds. Comprehensive Organometallic Chemistry II. Pergamon Press, Oxford, 1995
[10] Schumann H, Meese-Marktscheffel J A, Esser L. Chem Rev, 1995, 95: 865
[11] Wang C, Xi Z F. Chem Commun, 2007: 5119
[12] Komatsu K. Bull Chem Soc Jpn, 2001, 74: 407
[13] Hui C W, Mak T C W, Wong H N C. Tetrahedron, 2004, 60: 3523
[14] Lai C W, Lam C K, Lee H K, Mak T C W, Wong H N C. Org Lett, 2003, 5: 823
[15] Lawrie C J, Gable K P, Carpenter B K. Organometallics, 1989, 8: 2274
[16] Esser B, Bandyopadhyay A, Rominger F, Gleiter R. Chem Eur J, 2009, 15: 3368
[17] Carnes M, Buccella D, Decatur J, Steigerwald M L, Nuckolls C. Angew Chem Int Ed, 2008, 47: 2982
[18] Takahashi T, Sun W H, Nakajima K. Chem Commun, 1999: 1595
[19] Li G T, Fang H Y, Zhang S W, Xi Z F. Tetrahedron Lett, 2004, 45: 8399
[20] Wang C, Yuan J, Li G T, Wang Z T, Zhang S W, Xi Z F. J Am Chem Soc, 2006, 128: 4564
[21] Wei J N, Wang Z T, Zhang W X, Xi Z F. Org Lett, 2013, 15: 1222
[22] Geng W Z, Wei J N, Zhang W X, Xi Z F. J Am Chem Soc, 2014, 136: 610
[23] Yamamoto Y, Ohno T, Itoh K. Chem Commun, 1999: 1543
[24] Yamamoto Y, Ohno T, Itoh K. Chem Eur J, 2002, 8: 4734
[25] Chen C, Xi C J, Lai C B, Wang R J, Hong X Y. Eur J Org Chem, 2004: 647
[26] Wender P A, Christy J P. J Am Chem Soc, 2007, 129: 13402
[27] Wender P A, Christy J P, Lesser A B, Gieseler M T. Angew Chem Int Ed, 2009, 48: 7687
[28] Ubayama H, Sun W H, Takahashi T, Xi Z F. Chem Commun, 1998: 1931
[29] Eisch J J, Piotrowski A M, Han K I, Krüger C, Tsay Y H. Organometallics, 1985, 4: 224
[30] Edelbach B L, Lachicotte R J, Jones W D. J Am Chem Soc, 1998, 120: 2843
[31] Perthuisot C, Edelbach B L, Zubris D L, Simhai N, Iverson C N, Müller C, Satoh T, Jones W D. J Mol Catal A, 2002, 189: 157
[32] Masselot D, Charmant J P H, Gallagher T. J Am Chem Soc, 2006, 128: 694
[33] Schaub T, Backes M, Radius U. Organometallics, 2006, 25: 4196
[34] Ananikov V P, Hazipov O V, Beletskaya I P. Chem Asian J, 2011, 6: 306
[35] Negishi E, Cederbaum F E, Takahashi T. Tetrahedron Lett, 1986, 27: 2829
[36] Yasuike S, Ohta H, Shiratori S, Kurita J, Tsuchiya T. J Chem Soc, Chem Commun, 1993: 1817
[37] Teplý F, Stará I G, Starý I, Kollárovi? A, Šaman D, Rulíšek L, Fiedler P. J Am Chem Soc, 2002, 124: 9175
[38] Barluenga J, Valdés C, Beltrán G, Escribano M, Aznar F. Angew Chem Int Ed, 2006, 45: 6893
[39] Ball C J, Gilmore J, Willis M C. Angew Chem Int Ed, 2012, 51: 5718
[40] Muzalevskiy V M, Nenajdenko V G, Shastin A V, Balenkova E S, Haufe G. Synthesis, 2009: 2249
[41] Corey J C, John C S, Ohmsted M C, Chang L S. J Organomet Chem, 1986, 304: 93
[42] Liu Y X, Stringfellow T C, Ballweg D, Guzei I A, West R. J Am Chem Soc, 2002, 124: 49
[43] Chang L S, Corey J Y. Organometallics, 1989, 8: 1885
[44] Shimizu M, Tomioka Y, Nagao I, Kadowaki T, Hiyama T. Chem Asian J, 2012, 7: 1644
[45] Willis M C, Brace G N, Findlay T J K, Holmes I P. Adv Synth Catal, 2006, 348: 851
[46] Shen Q L, Hartwig J F. J Am Chem Soc, 2006, 128: 10028
[47] Liang Y, Meng T H, Zhang H J, Xi, Z F. Synlett, 2011: 911
[48] Tadd A C, Matsuno A, Fielding M R, Willis M C. Org Lett, 2009, 11: 583
[49] Kundu D, Maity P, Ranu B C. Org Lett, 2014, 16: 1040
[50] Geng W Z, Zhang W X, Hao W, Xi Z F. J Am Chem Soc, 2012, 134: 20230
[51] Fang H Y, Li G T, Mao G L, Xi Z F. Chem Eur J, 2004, 10: 3444
[52] Liang Y, Geng W Z, Wei J N, Ouyang K B, Xi Z F. Org Biomol Chem, 2012, 10: 1537
[53] Xi Z F. Acc Chem Res, 2010, 43: 1342
[54] Wei J N, Liu L, Zhan M, Xu L, Zhang W X, Xi Z F. Angew Chem Int Ed, 2014, 53: 5634
[55] Li H, Wei B S, Xu L, Zhang W X, Xi Z F. Angew Chem Int Ed, 2013, 52: 10822
[56] Zhou Y, Zhang W X, Xi Z F. Organometallics, 2012, 31: 5546
[57] Zhang H J, Wei J N, Zhao F, Liang Y, Wang Z T, Xi Z F. Chem Commun, 2010, 46: 7439
[58] Schaub T, Radius U. Chem Eur J, 2005, 11: 5024
[59] Sheldrick G M. SHELXTL 5.10 for Windows NT: Structure Determination Software Programs. Bruker Analytical X-ray Systems, Inc., Madison, WI, 1997
[60] Sheldrick G M. Acta Cryst A, 2008, 64: 112
[61] Dolomanov O V, Bourhis L J, Gildea R J, Howard J A K, Puschmann H. J Appl Cryst, 2009, 42: 339
[62] Ouyang K B, Xi Z F. Acta Chim Sin, 2013, 71: 13
[63] Hassan J, Hathroubi C, Gozzi C, Lemaire M. Tetrahedron, 2001, 57: 7845
[64] Hassan J, Penalva V, Lavenot L, Gozzi C, Lemaire M. Tetrahedron, 1998, 54: 13793
[65] Shao L J, Du Y J, Zeng M F, Li X D, Shen W T, Zuo S F, Lu Y Q, Zhang X M, Qi C Z. Appl Organometal Chem, 2010, 24: 421
[66] Nadri S, Azadi E, Ataei A, Joshaghani M, Rafiee E. J Organomet Chem, 2011, 696: 2966
[67] Sehnal P, Taylor R J K, Fairlamb I J S. Chem Rev, 2010, 110: 824
[68] Xu L M, Li B J, Yang Z, Shi Z J. Chem Soc Rev, 2010, 39: 712
[69] Mu X, Wu T, Wang H Y, Guo Y L, Liu G S. J Am Chem Soc, 2012, 134: 878
[70] Canty A J, Patel J, Rodemann T, Ryan J H, Skelton B W, White A H. Organometallics, 2004, 23: 3466