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Nickel‐Catalyzed 1,1‐Alkylboration of Electronically Unbiased Terminal Alkenes
Author(s) -
Li Yangyang,
Pang Hailiang,
Wu Dong,
Li Zheqi,
Wang Wang,
Wei Hong,
Fu Ying,
Yin Guoyin
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201903890
Subject(s) - catalysis , chemistry , regioselectivity , nickel , combinatorial chemistry , selectivity , ethylene , boron , functional group , substrate (aquarium) , bond cleavage , organic chemistry , oceanography , geology , polymer
An unprecedented nickel‐catalyzed 1,1‐alkylboration of electronically unbiased alkenes has been developed, providing straightforward access to secondary aliphatic boronic esters from readily available materials under very mild reaction conditions. The regioselectivity of this reaction is governed by a unique pyridyl carboxamide ligated catalyst, rather than the substrates. Moreover, this transformation shows excellent chemo‐ and regio‐selectivity and remarkably good functional‐group tolerance. We also demonstrate that under balloon pressure, ethylene can also be utilized as a substrate. Additionally, competence experiments indicate that selective bond formation is favored at the α‐position of boron and preliminary mechanistic studies indicate that the key step in this three‐component reaction involves a 1,2‐nickel migration.