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Multigram Synthesis and C−C/C−N Couplings of Functionalized 1,2‐Disubstituted Cyclopropyltrifluoroborates
Author(s) -
Hryschuk Oleksandr V.,
Yurov Yevhen,
Tymtsunik Andriy V.,
Kovtunenko Volodymyr O.,
Komarov Igor V.,
Grygorenko Oleksandr O.
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900879
Subject(s) - chemistry , diastereomer , diazo , combinatorial chemistry , catalysis , reaction conditions , organic chemistry
A convenient approach to the multigram synthesis of functionalized 1,2‐disubstituted cyclopropyltrifluoroborates was developed, based on Pd(II)‐ or Cu(I)‐catalyzed reaction of vinyltrifluoroborate and diazo compounds. Optimized protocols allowed for the preparation of the target products as pure diastereomers on multigram scale. It was shown that the title compounds were good coupling partners for the Suzuki‐Miyaura and Chan‐Lam reactions, which provide medicinally relevant (het)arylcyclopropanes with high diastereoselectivity.