Synthesis 2021; 53(02): 255-266
DOI: 10.1055/s-0040-1707270
short review

Cross-Coupling Reactions of Double or Triple Electrophilic Templates for Alkene Synthesis

Tereza Edlová
,
Marek Čubiňák
,
Tomáš Tobrman
Department of Organic Chemistry, University of Chemistry and Technology, Prague, Technická 5, 166 28 Prague 6, Czech Republic   Email: tomas.tobrman@vscht.cz
› Author Affiliations
This work was supported by the Grantová Agentura České Republiky (Grant Agency of the Czech Republic) (Grant No. 18-12150S) and the Ministerstvo Školství, Mládeže a Tělovýchovy (Ministry of Education, Youth and Sport) (Grant No. A2_FCHT_2020_023).


Abstract

This short review summarizes the latest advances in the cross-coupling reactions of double and triple electrophilic templates bearing halogen atoms and an activated C–O bond. Reactions involving the formation of a C–C bond as part of di-, tri-, and tetrasubstituted double bond systems are highlighted.

1 Introduction

2 Cross-Coupling Reactions of Halovinyl Tosylates

3 Cross-Coupling Reactions of Halovinyl Triflates

4 Cross-Coupling Reactions of Halovinyl Phosphates

5 Cross-Coupling Reactions of Halovinyl Esters

6 Conclusion



Publication History

Received: 16 June 2020

Accepted after revision: 04 August 2020

Article published online:
22 September 2020

© 2020. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
  • References

    • 1a Shang M, Sun S.-Z, Wang H.-L, Wang M.-M, Dai H.-X. Synthesis 2016; 48: 4381
    • 1b Moselage M, Li J, Ackermann L. ACS Catal. 2016; 6: 498
    • 1c Gensch T, Hopkinson MN, Glorius F, Wencel-Delord J. Chem. Soc. Rev. 2016; 45: 2900
    • 2a Wang Q, Su Y, Li L, Huang H. Chem. Soc. Rev. 2016; 45: 1257
    • 2b Meng G, Shi S, Szostak M. Synlett 2016; 27: 2530
    • 2c Zhu C, Wang R, Falck JR. Chem. Asian J. 2012; 7: 1502
    • 3a Song F, Gou T, Wang B.-Q, Shi Z.-J. Chem. Soc. Rev. 2018; 47: 7078
    • 3b Liang Y.-F, Jiao N. Acc. Chem. Res. 2017; 50: 1640
    • 3c Kim D.-S, Park W.-J, Jun C.-H. Chem. Rev. 2017; 117: 8977
    • 4a Cheng H.-G, Chen H, Liu Y, Zhou Q. Asian J. Org. Chem. 2018; 7: 490
    • 4b Pan F, Shi Z.-J. ACS Catal. 2014; 4: 280
    • 4c Prokopcová H, Kappe CO. Angew. Chem. Int. Ed. 2009; 48: 2276
  • 5 Wang L, Chen H, Duan Z. Chem. Asian J. 2018; 13: 2164
    • 7a Chen J, Chen S, Xu X, Tang Z, Au C.-T, Qiu R. J. Org. Chem. 2016; 81: 3246
    • 7b Lopez MJ, Kondo A, Nagae H, Yamamoto K, Tsurugi H, Mashima K. Organometallics 2016; 35: 3816
    • 7c Wang C, Teo WJ, Ge S. Nat. Commun. 2017; 8: 2258
    • 7d Manikandan R, Jeganmohan M. Org. Biomol. Chem. 2015; 13: 10420
    • 7e Mori M. Eur. J. Org. Chem. 2007; 4981
    • 7f Negishi E.-i, Huang Z, Wang G, Mohan S, Wang C, Hattori H. Acc. Chem. Res. 2008; 41: 1474
    • 8a Bakthadoss M, Raman S, Mushaf M. Org. Biomol. Chem. 2019; 17: 4767
    • 8b Han HS, Lee YJ, Jung Y.-S, Han SB. Org. Lett. 2017; 19: 1962
    • 8c Chen S, Xie S.-H, Ai C.-Y, Zhang X.-L. Tetrahedron Lett. 2019; 60: 1234
    • 8d Drouin M, Hamel J.-D, Paquin J.-F. Synthesis 2018; 50: 881
    • 8e Maraswami M, Loh T.-P. Synthesis 2019; 51: 1049
    • 8f Polák P, Váňová H, Dvořák D, Tobrman T. Tetrahedron Lett. 2016; 57: 3684
    • 9a Meshram HM, Reddy PN, Sadashiv K, Yadav JS. Tetrahedron Lett. 2005; 46: 623
    • 9b Meshram HM, Reddy PN, Vishnu P, Sadashiv K, Yadav JS. Tetrahedron Lett. 2006; 47: 991
  • 10 Jeevan Chakravarthy AS, Shahina Begum N, Krishnamurthy MS, HariPrasad S. Mol. Cryst. Liq. Cryst. 2019; 682: 65
  • 11 Boukouvalas J, McCann LC. Tetrahedron Lett. 2010; 51: 4636
  • 12 Takeda Y, Shimizu M, Hiyama T. Angew. Chem. Int. Ed. 2007; 46: 8659
  • 13 Masaki S, Youhei T, Tamejiro H. Bull. Chem. Soc. Jpn. 2011; 84: 1339
  • 14 Zhang H, Zhou C.-B, Chen Q.-Y, Xiao J.-C, Hong R. Org. Lett. 2011; 13: 560
  • 15 Kim SJ, Ryu HG, Jeon SL, Jeong IH. J. Fluorine Chem. 2017; 196: 67
  • 16 Lei X, Gao L, Ding Q, Peng Y, Wu J. Org. Biomol. Chem. 2011; 9: 6265
  • 17 Mondal K, Pan SC. Eur. J. Org. Chem. 2015; 2129
  • 18 Cahiez G, Moyeux A, Poizat M. Chem. Commun. 2014; 50: 8982
  • 19 Ashida Y, Nakata K, Yoshitake D, Sato Y, Miyazaki Y, Tanabe Y. Asian J. Org. Chem. 2020; 9: 604
  • 20 Kim JH, Jeong YR, Jeon SL, Jeong IH. J. Fluorine Chem. 2014; 167: 166
  • 21 Lee HY, Jeon JH, Jeon SL, Jeong IH. Bull. Korean Chem. Soc. 2012; 33: 379
  • 22 Wu J.-Q, Zhang S.-S, Gao H, Qi Z, Zhou C.-J, Ji W.-W, Liu Y, Chen Y, Li Q, Li X, Wang H. J. Am. Chem. Soc. 2017; 139: 3537
  • 23 Tian M, Yang X, Zhang B, Liu B, Li X. Org. Chem. Front. 2018; 5: 3406
  • 24 Song S, Liu H, Wang L, Zhu C, Loh T.-P, Feng C. Chin. J. Chem. 2019; 37: 1036
  • 25 Ji W.-W, Lin E, Li Q, Wang H. Chem. Commun. 2017; 53: 5665
  • 26 Blond G, Bour C, Salem B, Suffert J. Org. Lett. 2008; 10: 1075
  • 27 Hayashi R, Fernández S, Okamura WH. Org. Lett. 2002; 4: 851
  • 28 Sünnemann HW, Banwell MG, de Meijere A. Eur. J. Org. Chem. 2007; 3879
  • 29 Shi Y, Yang B, Cai S, Gao S. Angew. Chem. Int. Ed. 2014; 53: 9539
  • 30 He P, Wang Z. Org Chem. Front. 2018; 5: 2552
  • 31 Masters K.-S, Flynn BL. Adv. Synth. Catal. 2009; 351: 530
    • 32a Sünnemann HW, de Meijere A. Angew. Chem. Int. Ed. 2004; 43: 895
    • 32b Sünnemann HW, Hofmeister A, Magull J, de Meijere A. Chem. Eur. J. 2007; 13: 3739
    • 33a Chen Z.-M, Liu J, Guo J.-Y, Loch M, DeLuca RJ, Sigman MS. Chem. Sci. 2019; 10: 7246
    • 33b Patel HH, Sigman MS. J. Am. Chem. Soc. 2015; 137: 3462
    • 33c Zhang C, Tutkowski B, DeLuca RJ, Joyce LA, Wiest O, Sigman MS. Chem. Sci. 2017; 8: 2277
  • 34 von Essen R, von Zezschwitz P, Vidović D, de Meijere A. Chem.Eur. J. 2004; 10: 4341
  • 35 Ngo TN, Akrawi OA, Dang TT, Villinger A, Langer P. Tetrahedron Lett. 2015; 56: 86
  • 36 Azyat K, Jahnke E, Rankin T, Tykwinski RR. Chem. Commun. 2009; 433
  • 37 Lenz C, Haubmann C, Hübner H, Boeckler F, Gmeiner P. Bioorg. Med. Chem. 2005; 13: 185
  • 38 Rao ML. N, Kumar A. Tetrahedron 2015; 71: 5137
  • 39 Kydarov R, Ilaldinov IZ, Almena J, Monsees A, Riermeier TH. Tetrahedron Lett. 2005; 46: 7397
  • 40 Chernick ET, Börzsönyi G, Steiner C, Ammon M, Gessner D, Frühbeißer S, Gröhn F, Maier S, Tykwinski RR. Angew. Chem. Int. Ed. 2014; 53: 310
  • 41 Zhang L, Meng T, Fan R, Wu J. J. Org. Chem. 2007; 72: 7279
  • 42 Kotek V, Dvořáková H, Tobrman T. Org. Lett. 2015; 17: 608
  • 43 Kotek V, Polák P, Dvořáková H, Tobrman T. Eur. J. Org. Chem. 2016; 5037
  • 44 Polák P, Tobrman T. Eur. J. Org. Chem. 2019; 957
  • 45 Kawada H, Ikoma A, Ogawa N, Kobayashi Y. J. Org. Chem. 2015; 80: 9192
  • 46 Kazem Shiroodi R, Dudnik AS, Gevorgyan V. J. Am. Chem. Soc. 2012; 134: 6928
  • 47 Huang X, He Y, Ding Y. Phosphorus Sulfur Silicon Relat. Elem. 2001; 174: 201
  • 48 Ding Y, Huang X. Heteroatom Chem. 2003; 14: 304
  • 49 Chary BC, Kim S, Shin D, Lee PH. Chem. Commun. 2011; 47: 7851
  • 50 Priebbenow DL, Barbaro L, Baell JB. Org. Biomol. Chem. 2016; 14: 9622
  • 51 Wang Y, Lu B, Zhang L. Chem. Commun. 2010; 46: 9179
  • 52 Chen X, Chen D, Lu Z, Kong L, Zhu G. J. Org. Chem. 2011; 76: 6338
  • 53 Okamoto N, Miwa Y, Minami H, Takeda K, Yanada R. J. Org. Chem. 2011; 76: 9133
    • 54a Priebbenow DL, Gable RW, Baell J. J. Org. Chem. 2015; 80: 4412
    • 54b González-Liste PJ, León F, Arribas I, Rubio M, García-Garrido SE, Cadierno V, Pizzano A. ACS Catal. 2016; 6: 3056
    • 55a León F, Francos J, López-Serrano J, García-Garrido SE, Cadierno V, Pizzano A. Chem. Commun. 2019; 55: 786
    • 55b León F, González-Liste PJ, García-Garrido SE, Arribas I, Rubio M, Cadierno V, Pizzano A. J. Org. Chem. 2017; 82: 5852
  • 56 Francos J, Cadierno V. Synthesis 2019; 51: 3117
  • 57 Takagi K, Mimura H, Inokawa S. Bull. Chem. Soc. Jpn. 1984; 57: 3517
  • 58 González-Liste PJ, Francos J, García-Garrido SE, Cadierno V. J. Org. Chem. 2017; 82: 1507
  • 59 Chen Z, Huang G, Jiang H, Huang H, Pan X. J. Org. Chem. 2011; 76: 1134
  • 60 Okamoto N, Yanada R. J Org. Chem. 2012; 77: 3944
  • 61 Xia X.-F, Gu Z, Liu W, Wang N, Wang H, Xia Y, Gao H, Liu X. Org. Biomol. Chem. 2014; 12: 9909
  • 62 Chen Z.-W, Luo M.-T, Wen Y.-L, Ye M, Zhou Z.-G, Liu L.-X. Synlett 2014; 25: 2341
  • 63 Muthusamy G, Pansare SV. Org. Biomol. Chem. 2018; 16: 7971
  • 64 Jiang G, Li J, Zhu C, Wu W, Jiang H. Org. Lett. 2017; 19: 4440
  • 65 Wu J, Deng X, Hirao H, Yoshikai N. J. Am. Chem. Soc. 2016; 138: 9105