Investigation of the scope and mechanism of copper catalyzed regioselective methylthiolation of aryl halides

Methylthiolation of structurally diverse aryl halides was accomplished under fluoride free conditions using catalytic amounts of CuI, and DMSO as the methylthiolation source. Optimization studies unveiled several varieties of promoters among which Zn(OAc)2 was found ideal. The analogous reaction wit...

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Bibliographic Details
Published in:Tetrahedron 2013-09, Vol.69 (38), p.8276-8283
Main Authors: Joseph, P.J. Amal, Priyadarshini, S., Kantam, M. Lakshmi, Sreedhar, B.
Format: Article
Language:English
Subjects:
Aromatic compounds
Aryl halides
Aryl sulfides
Catalysis
Copper
CuSMe
Fluorides
Halides
Methylthiolation
Optimization
Purity
Tetrahedrons
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Summary:Methylthiolation of structurally diverse aryl halides was accomplished under fluoride free conditions using catalytic amounts of CuI, and DMSO as the methylthiolation source. Optimization studies unveiled several varieties of promoters among which Zn(OAc)2 was found ideal. The analogous reaction with DMSO-d6 afforded corresponding deuterated aryl methyl thioether with 99% purity. Mechanistic studies revealed CuSMe as the active methylthiolation agent. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2013.07.039