Catalyst Development in the Dehydrogenative Borylation of Alkenes for the Synthesis Vinylboronate Esters

Sida Li; Xin Cui; Yue Wang; Lipeng Wu

doi:10.1055/s-0040-1707275

Synlett, Inhaltsverzeichnis

Synlett 2021; 32(02): 102-108
DOI: 10.1055/s-0040-1707275

synpacts

Catalyst Development in the Dehydrogenative Borylation of Alkenes for the Synthesis Vinylboronate Esters

Sida Li

^aState Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou, 730000, P. R. of China eMail: lipengwu@licp.cas.cn

^bUniversity of Chinese Academy of Sciences, Beijing, 100049, P. R. of China

,

Xin Cui

^aState Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou, 730000, P. R. of China eMail: lipengwu@licp.cas.cn

,

Yue Wang

^aState Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou, 730000, P. R. of China eMail: lipengwu@licp.cas.cn

,

Lipeng Wu∗

^aState Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou, 730000, P. R. of China eMail: lipengwu@licp.cas.cn

^bUniversity of Chinese Academy of Sciences, Beijing, 100049, P. R. of China

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

Catalytic dehydrogenative borylation of alkenes provides an efficient and straightforward method for the preparation of synthetically useful vinylboronate esters. Here, we present a summary of developments and recent advances in this area, classified according to the various reactants and catalyst systems.

1 Introduction

2 Catalytic Dehydrogenative Borylation of Alkenes by Using Boranes

3 Catalytic Dehydrogenative Borylation of Alkenes by Using Diboranes

4 Zirconium-Catalyzed H^₂–Acceptorless Dehydrogenative Borylation of Alkenes with Boranes

5 Conclusion and Outlook

Key words

catalysis - borylation - dehydrogenation - vinylboronate esters - alkenes

Volltext

Referenzen

References
1 Carreras J, Caballero A, Pérez PJ. Chem. Asian J. 2019; 14: 329
2 Hilt G, Bolze P. Synthesis 2005; 2091

3a Fontani P, Carboni B, Vaultier M, Maas G. Synthesis 1991; 605
3b Carreras J, Caballero A, Pérez PJ. Angew. Chem. Int. Ed. 2018; 57: 2334

4 Livshits AB, Al Aziz Al Quntar A, Yekhtin Z, Srebnik M, Dagan A. Bioorg. Med. Chem. Lett. 2013; 23: 507
5 Brown HC, Bhat NG. Tetrahedron Lett. 1988; 29: 21
6 Gridnev ID, Miyaura N, Suzuki A. Organometallics 1993; 12: 589
7 Takagi J, Takahashi K, Ishiyama T, Miyaura N. J. Am. Chem. Soc. 2002; 124: 8001
8 Morrill C, Grubbs RH. J. Org. Chem. 2003; 68: 6031
9 Reid WB, Spillane JJ, Krause SB, Watson DA. J. Am. Chem. Soc. 2016; 138: 5539
10 Alonso DM, Bond JQ, Dumesic JA. Green Chem. 2010; 12: 1493
11 Geier SJ, Westcott SA. Rev. Inorg. Chem. 2014; 35: 69

12a Männig D, Nöth H. Angew. Chem. Int. Ed. 1985; 24: 878
12b Evans DA, Fu GC, Hoveyda AH. J. Am. Chem. Soc. 1992; 114: 6671
12c Yamamoto Y, Fujikawa R, Umemoto T, Miyaura N. Tetrahedron 2004; 60: 10695
12d Wu JY, Moreau B, Ritter T. J. Am. Chem. Soc. 2009; 131: 12915
12e Obligacion JV, Chirik PJ. Org. Lett. 2013; 15: 2680
12f Obligacion JV, Chirik PJ. J. Am. Chem. Soc. 2013; 135: 19107
12g Zhang L, Zuo Z, Leng X, Huang Z. Angew. Chem. Int. Ed. 2014; 53: 2696
12h Tseng K.-NT, Kampf JW, Szymczak NK. ACS Catal. 2014; 5: 411
12i Smith JR, Collins BS. L, Hesse MJ, Graham MA, Myers EL, Aggarwal VK. J. Am. Chem. Soc. 2017; 139: 9148
12j Chen X, Cheng Z, Lu Z. ACS Catal. 2019; 9: 4025
12k Wang G, Liang X, Chen L, Gao Q, Wang J.-G, Zhang P, Peng Q, Xu S. Angew. Chem. Int. Ed. 2019; 58: 8187
12l Vijaykumar G, Bhunia M, Mandal SK. Dalton Trans. 2019; 48: 5779

13 Davan T, Corcoran EW. Jr, Sneddon LG. Organometallics 1983; 2: 1693
14 Llynch AT, Sneddon LG. J. Am. Chem. Soc. 1989; 111: 6201
15 Brown JM, Lloyd-Jones GC. J. Chem. Soc., Chem. Commun. 1992; 710
16 Burgess K, Van der Donk WA, Westcott SA, Marder TB, Baker RT, Calabrese JC. J. Am. Chem. Soc. 1992; 114: 9350
17 Westcott SA, Marder TB, Baker RT. Organometallics 1993; 12: 975
18 Murata M, Watanabe S, Masuda Y. Tetrahedron Lett. 1999; 40: 2585
19 Brown AN, Zakharov LN, Mikulas T, Dixon DA, Liu S.-Y. Org. Lett. 2014; 16: 3340
20 Morimoto M, Miura T, Murakami M. Angew. Chem. Int. Ed. 2015; 54: 12659
21 Caballero A, Sabo-Etienne S. Organometallics 2007; 26: 1191
22 Wang C, Wu C, Ge S. ACS Catal. 2016; 6: 7585
23 Motry DH, Smith MR. III. J. Am. Chem. Soc. 1995; 117: 6615
24 Motry DH, Brazil AG, Smith MR. III. J. Am. Chem. Soc. 1997; 119: 2743
25 Neeve EC, Geier SJ, Mkhalid IA, Westcott SA, Marder TB. Chem. Rev. 2016; 116: 9091
26 Mkhalid IA, Coapes RB, Edes SN, Coventry DN, Souza FE, Thomas RL, Hall JJ, Bi SW, Lin Z, Marder TB. Dalton Trans. 2008; 1055
27 Kondoh A, Jamison TF. Chem. Commun. 2010; 46: 907
28 Olsson VJ, Szabó KJ. Angew. Chem. Int. Ed. 2007; 46: 6891
29 Sasaki I, Doi H, Hashimoto T, Kikuchi T, Ito H, Ishiyama T. Chem. Commun. 2013; 49: 7546
30 Takaya J, Kirai N, Iwasawa N. J. Am. Chem. Soc. 2011; 133: 12980
31 Kirai N, Iguchi S, Ito T, Takaya J, Iwasawa N. Bull. Chem. Soc. Jpn. 2013; 86: 784
32 Hu T.-J, Zhang G, Chen Y.-H, Feng C.-G, Lin G.-Q. J. Am. Chem. Soc. 2016; 138: 2897
33 Ohmura T, Takasaki Y, Furukawa H, Suginome M. Angew. Chem. Int. Ed. 2009; 48: 2372
34 Wen H, Zhang L, Zhu S, Liu G, Huang Z. ACS Catal. 2017; 7: 6419
35 Mazzacano TJ, Mankad NP. ACS Catal. 2017; 7: 146
36 Yoshii D, Jin X, Mizsuno N, Yamaguchi K. ACS Catal. 2019; 9: 3011

37a Tilley TD, Woo H.-G. In Inorganic and Organometallic Oligomers and Polymers . Harrod JF, Laine RM. Springer; Dordrecht: 1991: 3
37b Bourg S, Corriu RJ. P, Enders M, Moreau JJ. E. Organometallics 1995; 14: 564
37c Clark TJ, Russell CA, Manners I. J. Am. Chem. Soc. 2006; 128: 9582

38 Shi X, Li S, Wu L. Angew. Chem. Int. Ed. 2019; 58: 16167