TY - JOUR
T1 - Functionalization of [2.2]paracyclophanes via a reductive sulfanylation reaction
AU - Deschamps, Damien
AU - Lohier, Jean-François
AU - Richards, Christopher J.
AU - Gaumont, Annie-Claude
AU - Perrio, Stéphane
PY - 2021/1/1
Y1 - 2021/1/1
N2 - An expeditious route to planar chiral sulfur-based scaffolds has been achieved in two operational steps from cheap and commercial [2.2]paracyclophane hydrocarbon. The sulfur atom was introduced in a specific benzylic position of the [2.2]paracyclophane according to a reductive sulfanylation reaction, which proceeds under two complementary reaction conditions with either the BF3·OEt2/Et3SiH or TFA/BH3·THF combinations. The study was completed by the development of a highly efficient resolution approach by HPLC.
AB - An expeditious route to planar chiral sulfur-based scaffolds has been achieved in two operational steps from cheap and commercial [2.2]paracyclophane hydrocarbon. The sulfur atom was introduced in a specific benzylic position of the [2.2]paracyclophane according to a reductive sulfanylation reaction, which proceeds under two complementary reaction conditions with either the BF3·OEt2/Et3SiH or TFA/BH3·THF combinations. The study was completed by the development of a highly efficient resolution approach by HPLC.
UR - http://www.scopus.com/inward/record.url?scp=85098755506&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.0c02235
DO - 10.1021/acs.joc.0c02235
M3 - Article
VL - 86
SP - 507
EP - 514
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 1
ER -