Synthesis of β-Boryl-α-Aminosilanes by Copper-Catalyzed Aminoboration of Vinylsilanes

被引：65

作者：

Kato, Kodai ^{[1
]}

Hirano, Koji ^{[1
]}

Miura, Masahiro ^{[1
]}

机构：

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 46期

关键词：

alpha-aminosilanes; boron; copper; electrophilic amination; synthetic methods; C-H AMINATION; ELECTROPHILIC AMINATION; ASYMMETRIC-SYNTHESIS; COPPER(I)-CATALYZED REACTION; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; HYDROAMINATION; ARYL; ACIDS; HYDROXYLAMINES;

D O I：

10.1002/anie.201608139

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A copper-catalyzed regioselective and stereospecific aminoboration of vinylsilanes with bis(pinacolato)diboron (pinB-Bpin) and hydroxylamines has been developed. In the presence of a CuCl/MeO-dppbz catalyst, the boryl group and amino group are incorporated at the beta position and alpha position, respectively, and the corresponding beta-boryl-alpha-aminosilanes are obtained with good diastereoselectivity. The boryl group is a good latent functional group, and subsequent manipulations provide a variety of beta-functionalized alpha-aminosilanes of great potential in medicinal chemistry. Additionally, preliminary application to asymmetric catalysis is also described.

引用

页码：14398 / 14402

页数：5

共 50 条

[21] Copper-Catalyzed Highly Regioselective Silylcupration of Terminal Alkynes to Form α-Vinylsilanes
Wang, Peng
Yeo, Xue-Liang
Loh, Teck-Peng
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (05) : 1254 - 1256
[22] Copper-Catalyzed Regioselective Borocarbonylative Coupling of Unactivated Alkenes with Alkyl Halides: Synthesis of β-Boryl Ketones
Wu, Fu-Peng
Yuan, Yang
Schuenemann, Claas
Kamer, Paul C. J.
Wu, Xiao-Feng
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (26) : 10451 - 10455
[23] Copper-Catalyzed Simultaneous Installation of Boryl and Carbonyl Functionalities to Unsaturated Hydrocarbons
Fujihara, Tetsuaki
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (12)
[24] Copper-Catalyzed Enantioselective Aminoboration of Styrenes with 1,2-Benzisoxazole as Nitrogen Source
Huang Hao
Lin Huaxin
Wang Min
Liao Jian
ACTA CHIMICA SINICA, 2020, 78 (11) : 1229 - 1234
[25] Copper-catalyzed Hiyama cross-coupling using vinylsilanes and benzylic electrophiles
Cornelissen, L.
Cirriez, V.
Vercruysse, S.
Riant, O.
CHEMICAL COMMUNICATIONS, 2014, 50 (59) : 8018 - 8020
[26] Copper catalyzed borocarbonylation of benzylidenecyclopropanes through selective proximal C-C bond cleavage: synthesis of γ-boryl-γ,δ-unsaturated carbonyl compounds
Yang, Li-Miao
Zeng, Hui-Hui
Liu, Xin-Lian
Ma, Ai-Jun
Peng, Jin-Bao
CHEMICAL SCIENCE, 2022, 13 (24) : 7304 - 7309
[27] Copper-Catalyzed Cross-Coupling of Aryldiazoacetates with Bis[(pinacolato)boryl]methane
Bao, Zhicheng
Li, Muyao
Wang, Jianbo
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (05) : 1808 - 1814
[28] Copper-Catalyzed Umpolung of Imines through Carbon-to-Nitrogen Boryl Migration
Li, Zhenghua
Zhang, Liang
Nishiura, Masayoshi
Hou, Zhaomin
ACS CATALYSIS, 2019, 9 (05) : 4388 - 4393
[29] Copper-Catalyzed Carbonylative Synthesis of β-Boryl Amides via Boroamidation of Alkenes (vol 3, pg 2643, 2021)
Wu, F. P.
CCS CHEMISTRY, 2022, 4 (12): : 3895 - 3895
[30] Synthesis of 2-Boryl- and Silylindoles by Copper-Catalyzed Borylative and Silylative Cyclization of 2-Alkenylaryl Isocyanides
Tobisu, Mamoru
Fujihara, Hirokazu
Koh, Keika
Chatani, Naoto
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (14): : 4841 - 4847

← 1 2 3 4 5 →