Electrochemical Borylation of Electron-Deficient Alkenes and Allenoates

被引：7

作者：

Aelterman, Maude ^{[1
]}

Jubault, Philippe ^{[1
]}

Poisson, Thomas ^{[1
]}

机构：

[1] Normandie Univ, INSA Rouen, UNIROUEN, COBRA,UMR 6014,CNRS, F-76000 Rouen, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 26卷 / 17期

关键词：

allenoates; borylation; electrochemistry; electron-deficient alkenes; synthetic method; ALPHA; BETA-UNSATURATED CARBONYL-COMPOUNDS; CATALYZED BETA-BORATION; B BOND FORMATION; HYDROBORATION; ACTIVATION; CHEMISTRY; REAGENTS; TERTIARY; COMPLEX; AMIDE;

D O I：

10.1002/ejoc.202300063

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The electrochemical borylation of electro-deficient alkenes and allenoates is disclosed. In an undivided cell and under galvanostatic conditions a panel of Michael acceptor and allenoates was readily reacted. The reaction offered an access to versatile borylated building blocks in good to excellent yields (20 examples, 47 % to 91 % yields). A plausible reaction mechanism, based on the literature precedent was suggested.

引用

页数：4

共 50 条

[41] Reduction of Electron-Deficient Alkenes Enabled by a Photoinduced Hydrogen Atom Transfer
Larionova, Natalia A.
Ondozabal, Jun Miyatake
Cambeiro, Xacobe C.
ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (02) : 558 - 564
[42] Electrochemical O-trifluoromethylation of electron-deficient phenols
Bernd, Johannes
Werner, Philipp
Zeplichal, Marc
Terfort, Andreas
ELECTROCHEMISTRY COMMUNICATIONS, 2021, 133
[43] Nickel-catalysed cyclopropanation of electron-deficient alkenes with diiodomethane and diethylzinc
Xu, Jin
Samsuri, Nazurah Binte
Duong, Hung A.
CHEMICAL COMMUNICATIONS, 2016, 52 (16) : 3372 - 3375
[44] Arylsilylation of Electron-Deficient Alkenes via Cooperative Photoredox and Nickel Catalysis
Zhang, Zhikun
Hu, Xile
ACS CATALYSIS, 2020, 10 (01): : 777 - 782
[45] Iodo-Carbocyclization of Electron-Deficient Alkenes: Synthesis of Oxindoles and Spirooxindoles
Wei, Hai-Long
Piou, Tiffany
Dufour, Jeremy
Neuville, Luc
Zhu, Jieping
ORGANIC LETTERS, 2011, 13 (09) : 2244 - 2247
[46] Cooperative Catalytic Coupling of Benzyl Chlorides and Bromides with Electron-Deficient Alkenes
Hanumanthu, Roshini
Weaver, Jimmie D., III
ORGANIC LETTERS, 2024, 26 (25) : 5248 - 5252
[47] Reactions of diazo esters with electron-deficient alkenes in the presence of Lewis acids
R. A. Novikov
D. N. Platonov
V. A. Dokichev
Yu. V. Tomilov
O. M. Nefedov
Russian Chemical Bulletin, 2010, 59 : 984 - 990
[48] Electrochemical fluoro-selenenylation of electron-deficient olefins
Nagura, Hirokatsu
Inagi, Shinsuke
Fuchigami, Toshio
TETRAHEDRON, 2009, 65 (08) : 1559 - 1566
[49] Diastereoselective protonation on radical anions of electron-deficient alkenes via photoinduced electron transfer
Hayamizu, T
Maeda, H
Mizuno, K
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (15): : 4997 - 5004
[50] PHOTOSILYLATION OF ELECTRON-DEFICIENT ALKENES BY USE OF DISILANES VIA PHOTOINDUCED ELECTRON-TRANSFER
MIZUNO, K
NAKANISHI, K
CHOSA, J
NGUYEN, T
OTSUJI, Y
TETRAHEDRON LETTERS, 1989, 30 (28) : 3689 - 3692

← 1 2 3 4 5 →