Palladium-catalyzed azathiolation of carbon monoxide

Authors
Kuniyasu, H Hiraike, H Morita, M Tanaka, A Sugoh, K Kurosawa, H
Citation
H. Kuniyasu et al., Palladium-catalyzed azathiolation of carbon monoxide, J ORG CHEM, 64(20), 1999, pp. 7305-7308
Citations number
48
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
64
Issue
20
Year of publication
1999
Pages
7305 - 7308
Database
ISI
SICI code
0022-3263(19991001)64:20<7305:PAOCM>2.0.ZU;2-M
Abstract
A novel palladium-catalyzed azathiolation of carbon monoxide using sulfenam ide (RSNR'(2)) (1) is described to provide thiocarbamate 2 in good yields. The mechanistic proposal includes the following: (1) insertion of CO into P d-S bond of Pd(SR)(2)(PPh3)(n) 4 to provide Pd[C(O)SR](SR)-(PPh3)(n) 5 and (2) sigma-bond metathesis between S-N and Pd-C(O) bonds to afford 2 with th e regeneration of 4.