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Multigram Synthesis and C−C/C−N Couplings of Functionalized 1,2‐Disubstituted Cyclopropyltrifluoroborates

Adv. Synth. Catal. 2019, 361 (23), 5428-5439

DOI: 10.1002/adsc.201900879

Hryshchuk O.; Yurov Y.; Tymtsunik A.; Kovtunenko V.; Komarov I.; Grygorenko O.

A convenient approach to multigram synthesis of functionalized 1,2‐disubstituted cyclopropyltrifluoroborates is developed, which is based on Pd(II)‐ or Cu(I)‐catalyzed reaction of vinyl trifluoroborate 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.

Multigram Synthesis and C−C/C−N Couplings of Functionalized 1,2‐Disubstituted Cyclopropyltrifluoroborates

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