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Synthesis of trans-2-(trifluoromethyl)cyclopropanes via Suzuki Reactions With an N-methyliminodiacetic Acid Boronate

Matthew A J Duncton, Rajinder Singh

Org Lett. 2013 Sep 6;15(17):4284-7.

PMID: 23952128

Abstract:

trans-2-(Trifluoromethyl)cyclopropylboronic acid N-methyliminodiacetic acid (MIDA) ester 5 was synthesized as a pure diastereomer from vinylboronic acid MIDA ester and (trifluoromethyl)diazomethane in a single step. An X-ray study confirmed the trans-stereochemistry around the cyclopropyl ring. Use of 5 in Suzuki reactions, with a variety of aryl or heteroaryl coupling partners, provided trans-2-(trifluoromethyl)cyclopropyl products in moderate to excellent yields (17-90%).

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP1104636738 Vinylboronic acid MIDA ester Vinylboronic acid MIDA ester 1104636-73-8 Price
AP1104637366 Cyclopropylboronic acid MIDA ester Cyclopropylboronic acid MIDA ester 1104637-36-6 Price
AP1105069279 cis-2-Bromovinylboronic acid MIDA ester cis-2-Bromovinylboronic acid MIDA ester 1105069-27-9 Price
AP117311849 Cyclopentylboronic acid MIDA ester Cyclopentylboronic acid MIDA ester 117311-84-9 Price
AP1227700426 6-Methyl-2-pyridinylboronic acid MIDA ester 6-Methyl-2-pyridinylboronic acid MIDA ester 1227700-42-6 Price
LS7931335 1-Naphthylboronic acid MIDA ester 1-Naphthylboronic acid MIDA ester Price
LS7931390 2-trifluoromethoxyphenylboronic acid MIDA ester 2-trifluoromethoxyphenylboronic acid MIDA ester Price
LS7931391 3-trifluoromethoxyphenylboronic acid MIDA ester 3-trifluoromethoxyphenylboronic acid MIDA ester Price
LS7931392 trans-3-Phenyl-1-propen-1-ylboronic acid MIDA ester trans-3-Phenyl-1-propen-1-ylboronic acid MIDA ester Price
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