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Iodine‐Mediated Copper‐Catalyzed Efficient α ‐C( sp 2 )‐Thiomethylation of α ‐Oxoketene Dithioacetals with Dimethyl Sulfoxide in One Pot
Author(s) -
Shukla Gaurav,
Srivastava Abhijeet,
Nagaraju Anugula,
Raghuvanshi Keshav,
Singh Maya Shankar
Publication year - 2015
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.201500634
Subject(s) - chemistry , dimethyl sulfoxide , reagent , halogenation , iodine , solvent , salt (chemistry) , catalysis , copper , sulfoxide , medicinal chemistry , organic chemistry , combinatorial chemistry , inorganic chemistry
The direct α‐C sp 2 H functionalization and thiomethylation of α‐oxoketene dithioacetals (DTAs) has been accomplished with dimethyl sulfoxide (DMSO) in the presence of iodine and a copper(I) salt for the first time. A prerequisite is the in situ iodination of the α‐C sp 2 atom of dithioacetals that could offer other reaction channels. The operationally simple one‐pot protocol includes region‐defined consecutive iodination and sulfenylation of the challenging α‐C sp 2 H bond of dithioacetals employing cheap and readily available reagents. DMSO here plays a dual role as thiomethyl source and solvent.