Transition-Metal-Catalyzed Alkyl Heck-Type Reactions

Daria Kurandina; Padon Chuentragool; Vladimir Gevorgyan

doi:10.1055/s-0037-1611659

Synthesis, Table of Contents

CC BY ND NC 4.0 · Synthesis 2019; 51(05): 985-1005
DOI: 10.1055/s-0037-1611659

review

Copyright with the author

Transition-Metal-Catalyzed Alkyl Heck-Type Reactions

Daria Kurandina ‡

,

Padon Chuentragool ‡

,

Vladimir Gevorgyan *

Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL 60607-7061, USA Email: vlad@uic.edu

› Author Affiliations

Abstract

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Published as part of the 50 Years SYNTHESIS – Golden Anniversary Issue

‡ These authors contributed equally.

Abstract

The Heck reaction is one of the most reliable and useful strategies for the construction of C–C bonds in organic synthesis. However, in contrast to the well-established aryl Heck reaction, the analogous reaction employing alkyl electrophiles is much less developed. Significant progress in this area was recently achieved by merging radical-mediated and transition-metal-catalyzed approaches. This review summarizes the advances in alkyl Heck-type reactions from its discovery early in the 1970s up until the end of 2018.

1 Introduction

2 Pd-Catalyzed Heck-Type Reactions

2.1 Benzylic Electrophiles

2.2 α-Carbonyl Alkyl Halides

2.3 Fluoroalkyl Halides

2.4 α-Functionalized Alkyl Halides

2.5 Unactivated Alkyl Electrophiles

3 Ni-Catalyzed Heck-Type Reactions

3.1 Benzylic Electrophiles

3.2 α-Carbonyl Alkyl Halides

3.3 Unactivated Alkyl Halides

4 Co-Catalyzed Heck-Type Reactions

5 Cu-Catalyzed Heck-Type Reactions

6 Other Metals in Heck-Type Reactions

7 Conclusion

Key words

Heck reaction - cross-coupling - alkyl halides - alkenes - transition-metal catalysis

Full Text

References

References

1a Oestreich M. The Mizoroki-Heck Reaction . John Wiley & Sons; Chichester: 2009
1b Gharpure SJ, Shelke YG, Reddy SR. B. RSC Adv. 2014; 4: 46962
1c Heck RF. J. Am. Chem. Soc. 1969; 91: 6707
1d Heck RF, Nolley JP. J. Org. Chem. 1972; 37: 2320
1e Dieck HA, Heck RF. J. Am. Chem. Soc. 1974; 96: 1133
1f Mizoroki T, Mori K, Ozaki A. Bull. Chem. Soc. Jpn. 1971; 44: 581

2 de Meijere A, Bräse S, Oestreich M. Metal-Catalyzed Cross-Coupling Reactions and More . Wiley-VCH; Weinheim: 2014

3a Biajoli AF. P, Schwalm CS, Limberger J, Claudino TS, Monteiro AL. J. Braz. Chem. Soc. 2014; 25: 2186
3b Torborg C, Beller M. Adv. Synth. Catal. 2009; 351: 3027
3c de Vries JG. Can. J. Chem. 2001; 79: 1086
3d Majid MH, Razieh M, Masoumeh M. Curr. Org. Chem. 2018; 22: 165

4 Roy D, Uozumi Y. Adv. Synth. Catal. 2018; 360: 602
5 Wang S.-S, Yang G.-Y. Catal. Sci. Technol. 2016; 6: 2862
6 McCartney D, Guiry PJ. Chem. Soc. Rev. 2011; 40: 5122

7a Beletskaya IP, Cheprakov AV. Chem. Rev. 2000; 100: 3009
7b Cabri W, Candiani I. Acc. Chem. Res. 1995; 28: 2
7c Whitcombe NJ, Hii KK, Gibson SE. Tetrahedron 2001; 57: 7449
7d de Meijere A, Meyer FE. Angew. Chem. Int. Ed. 1995; 33: 2379

8 Ariafard A, Lin Z. Organometallics 2006; 25: 4030

9a Frisch AC, Beller M. Angew. Chem. Int. Ed. 2005; 44: 674
9b Tang S, Liu K, Liu C, Lei A. Chem. Soc. Rev. 2015; 44: 1070
9c Rudolph A, Lautens M. Angew. Chem. Int. Ed. 2009; 48: 2656

10a Phapale VB, Buñuel E, García-Iglesias M, Cárdenas DJ. Angew. Chem. Int. Ed. 2007; 46: 8790
10b Schley ND, Fu GC. J. Am. Chem. Soc. 2014; 136: 16588

11a Newcomb M, Toy PH. Acc. Chem. Res. 2000; 33: 449
11b Baldwin JE. Chem. Rev. 2003; 103: 1197

12a Wang C, Lei Y, Guo M, Shang Q, Liu H, Xu Z, Wang R. Org. Lett. 2017; 19: 6412
12b Fan J.-H, Wei W.-T, Zhou M.-B, Song R.-J, Li J.-H. Angew. Chem. Int. Ed. 2014; 53: 6650
12c Kancherla R, Muralirajan K, Maity B, Zhu C, Krach PE, Cavallo L, Rueping M. Angew. Chem. Int. Ed. 2019;

13 Yi P, Zhuangyu Z, Hongwen H. Synthesis 1995; 245
14 Higuchi K, Sawada K, Nambu H, Shogaki T, Kita Y. Org. Lett. 2003; 5: 3703
15 Wang L, Pan Y, Jiang X, Hu H. Tetrahedron Lett. 2000; 41: 725
16 Hu Y.-m, Zhou J, Long X.-t, Han J.-l, Zhu C.-j, Pan Y. Tetrahedron Lett. 2003; 44: 5009
17 Nagayama K, Shimizu I, Yamamoto A. Bull. Chem. Soc. Jpn. 1999; 72: 799
18 Narahashi H, Yamamoto A, Shimizu I. Chem. Lett. 2004; 33: 348
19 Yang Z, Zhou J. J. Am. Chem. Soc. 2012; 134: 11833
20 Wu GZ, Lamaty F, Negishi E. J. Org. Chem. 1989; 54: 2507
21 Liu Z, Shi C, Chen Y. Synlett 2008; 1734
22 Zhou W, An G, Zhang G, Han J, Pan Y. Org. Biomol. Chem. 2011; 9: 5833

23a Mori M, Oda I, Ban Y. Tetrahedron Lett. 1982; 23: 5315
23b Mori M, Kanda N, Oda I, Ban Y. Tetrahedron 1985; 41: 5465

24 Glorius F. Tetrahedron Lett. 2003; 44: 5751
25 Kurandina D, Rivas M, Radzhabov M, Gevorgyan V. Org. Lett. 2018; 20: 357
26 Chen Q.-Y, Yang Z.-Y, Zhao C.-X, Qiu Z.-M. J. Chem. Soc., Perkin Trans. 1 1988; 563
27 Surapanich N, Kuhakarn C, Pohmakotr M, Reutrakul V. Eur. J. Org. Chem. 2012; 5943
28 Feng Z, Min Q.-Q, Zhao H.-Y, Gu J.-W, Zhang X. Angew. Chem. Int. Ed. 2015; 54: 1270
29 Fan T, Meng W.-D, Zhang X. Beilstein J. Org. Chem. 2017; 13: 2610
30 Parasram M, Iaroshenko VO, Gevorgyan V. J. Am. Chem. Soc. 2014; 136: 17926
31 Kurandina D, Parasram M, Gevorgyan V. Angew. Chem. Int. Ed. 2017; 56: 14212

32a Bräse S, Waegell B, de Meijere A. Synthesis 1998; 148
32b Firmansjah L, Fu GC. J. Am. Chem. Soc. 2007; 129: 11340

33 Bloome KS, McMahen RL, Alexanian EJ. J. Am. Chem. Soc. 2011; 133: 20146
34 Bloome KS, Alexanian EJ. J. Am. Chem. Soc. 2010; 132: 12823
35 Venning AR. O, Kwiatkowski MR, Roque Peña JE, Lainhart BC, Guruparan AA, Alexanian EJ. J. Am. Chem. Soc. 2017; 139: 11595
36 Dong X, Han Y, Yan F, Liu Q, Wang P, Chen K, Li Y, Zhao Z, Dong Y, Liu H. Org. Lett. 2016; 18: 3774
37 McMahon CM, Alexanian EJ. Angew. Chem. Int. Ed. 2014; 53: 5974
38 Zou YJ, Zhou JR. Chem. Commun. 2014; 50: 3725
39 Wang G.-Z, Shang R, Cheng W.-M, Fu Y. J. Am. Chem. Soc. 2017; 139: 18307
40 Gevorgyan V, Chuentragool P, Yadagiri D, Morita T, Sarkar S, Parasram M, Wang Y. Angew. Chem. Int. Ed. 2019;
41 Teng S, Tessensohn ME, Webster RD, Zhou JS. ACS Catal. 2018; 8: 7439

42a Wang G.-Z, Shang R, Fu Y. Org. Lett. 2018; 20: 888
42b Koy M, Sandfort F, Tlahuext-Aca A, Quach L, Daniliuc CG, Glorius F. Eur. J. Chem. 2018; 24: 4552

43 Matsubara R, Jamison TF. J. Am. Chem. Soc. 2010; 132: 6880
44 Matsubara R, Gutierrez AC, Jamison TF. J. Am. Chem. Soc. 2011; 133: 19020
45 Standley EA, Jamison TF. J. Am. Chem. Soc. 2013; 135: 1585
46 Harris MR, Konev MO, Jarvo ER. J. Am. Chem. Soc. 2014; 136: 7825
47 Yu H, Hu B, Huang H. J. Org. Chem. 2018; 83: 13922
48 Liu C, Tang S, Liu D, Yuan J, Zheng L, Meng L, Lei A. Angew. Chem. Int. Ed. 2012; 51: 3638
49 Lebedev SA, Lopatina VS, Petrov ES, Beletskaya IP. J. Organomet. Chem. 1988; 344: 253
50 Millán A, Álvarez de Cienfuegos L, Miguel D, Campaña AG, Cuerva JM. Org. Lett. 2012; 14: 5984
51 Kwiatkowski MR, Alexanian EJ. Angew. Chem. Int. Ed. 2018; 57: 16857
52 Okabe M, Abe M, Tada M. J. Org. Chem. 1982; 47: 1775
53 Busato S, Tinembart O, Zhang Z.-D, Scheffold R. Tetrahedron 1990; 46: 3155

54a Giese B, Erdmann P, Göbel T, Springer R. Tetrahedron Lett. 1992; 33: 4545
54b Torii S, Inokuchi T, Yukawa T. J. Org. Chem. 1985; 50: 5875
54c Ladlow M, Pattenden G. Tetrahedron Lett. 1984; 25: 4317

55a Branchaud BP, Meier MS, Choi Y. Tetrahedron Lett. 1988; 29: 167
55b Branchaud BP, Yu GX. Organometallics 1993; 12: 4262
55c Branchaud BP, Detlefsen WD. Tetrahedron Lett. 1991; 32: 6273
55d Branchaud BP, Meier MS. J. Org. Chem. 1989; 54: 1320
55e Branchaud BP, Choi YL. Tetrahedron Lett. 1988; 29: 6037
55f Branchaud BP, Meier MS. Tetrahedron Lett. 1988; 29: 3191

56a Ikeda Y, Nakamura T, Yorimitsu H, Oshima K. J. Am. Chem. Soc. 2002; 124: 6514
56b Affo W, Ohmiya H, Fujioka T, Ikeda Y, Nakamura T, Yorimitsu H, Oshima K, Imamura Y, Mizuta T, Miyoshi K. J. Am. Chem. Soc. 2006; 128: 8068

57 Ikeda Y, Yorimitsu H, Shinokubo H, Oshima K. Adv. Synth. Catal. 2004; 346: 1631
58 Weiss ME, Kreis LM, Lauber A, Carreira EM. Angew. Chem. Int. Ed. 2011; 50: 11125
59 Kreis LM, Krautwald S, Pfeiffer N, Martin RE, Carreira EM. Org. Lett. 2013; 15: 1634
60 Cao H, Jiang H, Feng H, Kwan JM. C, Liu X, Wu J. J. Am. Chem. Soc. 2018; 140: 16360
61 Liwosz TW, Chemler SR. Org. Lett. 2013; 15: 3034
62 Nishikata T, Noda Y, Fujimoto R, Sakashita T. J. Am. Chem. Soc. 2013; 135: 16372
63 Nishikata T, Itonaga K, Yamaguchi N, Sumimoto M. Org. Lett. 2017; 19: 2686
64 Zhang X, Yi H, Liao Z, Zhang G, Fan C, Qin C, Liu J, Lei A. Org. Biomol. Chem. 2014; 12: 6790

65a Yang F, Fu SY, Chu W, Li C, Tong DG. RSC Adv. 2014; 4: 45838
65b Fu SY, Li YZ, Chu W, Lia C, Tong DG. Catal. Sci. Technol. 2015; 5: 1638

66 Tang C, Zhang R, Zhu B, Fu J, Deng Y, Tian L, Guan W, Bi X. J. Am. Chem. Soc. 2018; 140: 16929
67 Terao J, Watabe H, Miyamoto M, Kambe N. Bull. Chem. Soc. Jpn. 2003; 76: 2209
68 Liu Q, Yi H, Liu J, Yang Y, Zhang X, Zeng Z, Lei A. Eur. J. Chem. 2013; 19: 5120
69 Yu C, Iqbal N, Park S, Cho EJ. Chem. Commun. 2014; 50: 12884
70 Waldhart GW, Mankad NP. J. Organomet. Chem. 2015; 793: 171
71 Zhu N, Zhao J, Bao H. Chem. Sci. 2017; 8: 2081
72 Zong Z, Wang W, Bai X, Xi H, Li Z. Asian J. Org. Chem. 2015; 4: 622
73 Xie J, Li J, Weingand V, Rudolph M, Hashmi AS. K. Eur. J. Chem. 2016; 22: 12646