Dual Function of N-Iodosuccinimide for C(sp3)-B Bond Activation

被引：1

作者：

Youn, Ju Hyun ^{[1
]}

Go, Su Yong ^{[1
]}

Chung, Hyunho ^{[1
]}

Lee, Haeyeon ^{[1
]}

Chung, Taek Dong ^{[1
,2
]}

Cheong, Paul Ha-Yeon ^{[3
]}

Lee, Hong Geun ^{[1
]}

机构：

[1] Seoul Natl Univ, Coll Nat Sci, Dept Chem, Seoul 08826, South Korea

[2] Adv Inst Convergence Technol, Suwon 16229, Gyeonggi Do, South Korea

[3] Oregon State Univ, Dept Chem, Corvallis, OR 97331 USA

来源：

ORGANIC LETTERS | 2023年 / 26卷 / 01期

基金：

新加坡国家研究基金会;

关键词：

BORONIC ESTERS; C-H; OXIDATIVE AMINATION; SECONDARY; ACIDS; EFFICIENT; FUNCTIONALIZATION; TRANSFORMATIONS; GENERATION; CHEMISTRY;

D O I：

10.1021/acs.orglett.3c03728

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical method for C(sp(3))-B bond activation was developed. Using a combination of alkyl trifluoroborates and N-iodosuccinimide (NIS), various C(sp(3))-heteroatom bonds were readily generated in an efficient manner. Mechanistic studies revealed the bifunctional ability of NIS: mediating the formation of reactive halogenated intermediates and activating them via halogen bonding. This electrophilic activation of the reaction center enables the utilization of general heteroatom nucleophiles, which are used in a limited capacity in traditional 1,2-metalate rearrangements.

引用

页码：198 / 203

页数：6

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