Tris(pentafluorophenyl)borane-Catalyzed Stereospecific Bromocyanation of Styrene Derivatives with Cyanogen Bromide

被引：2

作者：

Kiyokawa, Kensuke ^{[1
]}

Noguchi, Ikumi ^{[1
]}

Nagata, Takaya ^{[1
]}

Minakata, Satoshi ^{[1
]}

机构：

[1] Osaka Univ, Dept Appl Chem, Grad Sch Engn, Suita, Osaka 5650871, Japan

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 14期

关键词：

NICKEL-CATALYZED CARBOCYANATION; INTRAMOLECULAR AMINOCYANATION; ELECTROPHILIC CYANATION; C-C; ALKENES; CYANIDE; PALLADIUM; ACTIVATION; INTERCONVERSION; HYDROCYANATION;

D O I：

10.1021/acs.orglett.3c00727

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We, herein, report on the bromocyanation of styrene derivatives with cyanogen bromide in the presence of tris(pentafluorophenyl)borane which functions as a Lewis acid catalyst that can effectively activate cyanogen bromide. This reaction proceeds through a stereospecific syn-addition. The protocol is operationally simple and provides practical access to beta-bromonitriles.

引用

页码：2537 / 2542

页数：6

共 43 条

[41] Strong Influence of the Nucleophile on the Rate and Selectivity of 1,2-Epoxyoctane Ring Opening Catalyzed by Tris(pentafluorophenyl)borane, B(C6F5)3
Bennett, Charmaine K.
Bhagat, Mihir N.
Zhu, Youlong
Yu, Ying
Raghuraman, Arjun
Belowich, Matthew E.
Nguyen, SonBinh T.
Notestein, Justin M.
Broadbelt, Linda J.
ACS CATALYSIS, 2019, 9 (12) : 11589 - 11602
[42] Rapid and Highly Selective Epoxidation of Styrene by meta-Chloroperbenzoic Acid Catalyzed by Manganese Meso-tetrakis(Pentafluorophenyl)Porphyrin in the Presence of Tetrabutylammonium Acetate and Bromide
Solati, Zahra
Hashemi, Majid
Ebrahimi, Leila
CATALYSIS LETTERS, 2011, 141 (01) : 163 - 167
[43] Rapid and Highly Selective Epoxidation of Styrene by meta-Chloroperbenzoic Acid Catalyzed by Manganese Meso-tetrakis(Pentafluorophenyl)Porphyrin in the Presence of Tetrabutylammonium Acetate and Bromide
Zahra Solati
Majid Hashemi
Leila Ebrahimi
Catalysis Letters, 2011, 141 : 163 - 167

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