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Copper‐Catalyzed Monoorganylation of Trialkyl Borates with Functionalized Organozinc Pivalates
Author(s) -
Fu Ying,
Gou BeiLei,
Shi ChunZhao,
Du Zhengyin,
Shen Tong
Publication year - 2018
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201800939
Subject(s) - reagent , chemistry , halide , boron , catalysis , boronic acid , organic chemistry , organometallic chemistry , copper , suzuki reaction , group 2 organometallic chemistry , combinatorial chemistry , molecule , palladium
Organozinc pivalates, a recently developed air‐ and moisture‐stable organozinc species, were found for the first time as excellent organometallic species in the monoorganylation of trialkyl borates whereby boronic acids were prepared in high yields. The significant advantage of organozinc pivalates over another previously employed organometallic reagents, e. g., organolithium reagents, Grignard reagents and organozinc halides, is that the generation of multiorganylation byproducts such as borinic acids and trialkylboranes were completely suppressed. Additionally, the in situ generated boronates could be directly arranged into Suzuki‐Miyaura type cross‐coupling reactions to produce biaryls in high yields.