Open AccessDealkenylative Thiylation of C(sp3)–C(sp2) Bonds
Author(s) -
Andrew J. Smaligo,
Ohyun Kwon
Publication year - 2019
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.9b03186
Subject(s) - chemistry , alkene , bond cleavage , molecule , cleavage (geology) , triple bond , carbon fibers , stereochemistry , organic chemistry , double bond , catalysis , materials science , geotechnical engineering , fracture (geology) , composite number , engineering , composite material
Carbon-carbon bond fragmentations are useful methods for the functionalization of molecules. The value of such cleavage events is maximized when paired with subsequent bond formation. Herein we report a protocol for the cleavage of an alkene C(sp 3 )-C(sp 2 ) bond, followed by the formation of a new C(sp 3 )-S bond. This reaction is performed in nonanhydrous solvent and open to the air, employs common starting materials, and can be used to rapidly diversify natural products.