Photochemical Radical C-H Halogenation of Benzyl N-Methyliminodiacetyl (MIDA) Boronates: Synthesis of α-Functionalized Alkyl Boronates
Photochemical Radical C-H Halogenation of Benzyl N-Methyliminodiacetyl (MIDA) Boronates: Synthesis of α-Functionalized Alkyl Boronates
复制标题
N-甲基亚氨基二乙酰苄基 (MIDA) 硼酸酯的光化学自由基 C-H 卤化：α-官能化烷基硼酸酯的合成。
DOI：
10.1002/anie.202011872
复制
发表时间：
2020-12-15
影响因子：
16.6
通讯作者：
Wang, Honggen
中科院分区：
文献类型：
--
作者：
Yang, Ling;Tan, Dong-Hang;Wang, Honggen
α-卤代硼酸盐是有用的有机硼酸盐，其可以转化为各种α-取代的烷基硼。制备α-卤代硼酸盐的方法是有限的，并且经常遭受苛刻的反应条件。本文报道了N-甲基亚氨基二乙酰基（MIDA）硼酸苄酯的光化学自由基C-H卤化。氟化，氯化，溴化反应是有效的，通过使用该协议。在与不同亲核试剂反应时，溴化产物中的C-Br键可以容易地转化为一系列C-C、C-O、C-N、C-S、C-P和C-I键，其中一些难以用α-卤代sp（2）-B硼酸酯伪造。发现了B（MIDA）部分的活化作用。
alpha-Haloboronates are useful organic synthons that can be converted to a diverse array of alpha-substituted alkyl borons. Methods to alpha-haloboronates are limiting and often suffer from harsh reaction conditions. Reported herein is a photochemical radical C-H halogenation of benzyl N-methyliminodiacetyl (MIDA) boronates. Fluorination, chlorination, and bromination reactions were effective by using this protocol. Upon reaction with different nucleophiles, the C-Br bond in the brominated product could be readily transformed to a series of C-C, C-O, C-N, C-S, C-P, and C-I bonds, some of which are difficult to forge with alpha-halo sp(2)-B boronate esters. An activation effect of B(MIDA) moiety was found.