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A Transition‐Metal‐Free and Base‐Mediated Carbene Insertion into Sulfur‐Sulfur and Selenium‐Selenium Bonds: An Easy Access to Thio‐ and Selenoacetals
Author(s) -
Arunprasath Dhanarajan,
Sekar Govindasamy
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201600855
Subject(s) - carbene , chemistry , selenium , sulfur , ylide , thio , insertion reaction , combinatorial chemistry , polymer chemistry , organic chemistry , catalysis
Abstract A transition‐metal‐free and base‐mediated carbene insertion across sulfur‐sulfur and selenium‐selenium bonds has been developed by employing N ‐tosylhydrazone as a stable and safe carbene precursor. The ylide formation from carbene followed by Stevens rearrangement are considered to be the key steps. This thiol and selenol‐free protocol delivers thioacetals and selenoacetals in good to excellent yields in short reaction time with good functional group tolerance. A one‐pot synthesis involving in situ generation of tosylhydrazone has also been demonstrated.