Photoinduced Transition-Metal-Free Alkynylation of Alkyl Pinacol Boronates

被引：35
|
作者：
Shi, Dunfa [1 ,2 ]
Xia, Chungu [1 ]
Liu, Chao [1 ]
机构：
[1] Chinese Acad Sci, Suzhou Res Inst, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat,CAS Key L, Lanzhou 730000, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
来源：
CCS CHEMISTRY | 2021年 / 3卷 / 06期
基金：
中国国家自然科学基金;
关键词：
organoboron; photocatalysis; C-C coupling; radical; synthetic methods; BORONIC ESTERS; ATE-COMPLEXES; VINYLIC ORGANOBORANES; GENERAL-SYNTHESIS; CHIRAL SYNTHESIS; PHOTOREDOX CATALYSIS; CONVENIENT SYNTHESIS; COUPLING REACTIONS; KETONES; SECONDARY;
D O I：
10.31635/ccschem.020.202000371
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An unprecedented visible-light-induced transition-metal-free alkynylation of alkyl pinacol boronates has been demonstrated with alkynyl phenylsulfones as the alkynylation reagents and 4CzIPN as the organic photocatalyst. Common sodium methoxide (NaOMe) or sodium hydroxide (NaOH) was used as the Lewis base togeneratephotoactivetetra-coordinatedboron species. Various functional groupswerewell tolerated. The selective monoalkynylation of diboronates was achieved to keep one boryl group in the product for potential further transformations. Radical trapping experiments and electron paramagnetic resonance (EPR) analysis confirmed the generation of alkyl radical intermediate.
引用
收藏
页码：1718 / 1728
页数：11
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