Iodine‐Mediated Copper‐Catalyzed Efficient  α ‐C( sp  2 )‐Thiomethylation of  α ‐Oxoketene Dithioacetals with Dimethyl Sulfoxide in One Pot | Zendy

Shukla Gaurav | Zendy; Srivastava Abhijeet | Zendy; Nagaraju Anugula | Zendy; Raghuvanshi Keshav | Zendy; Singh Maya Shankar | Zendy

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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.

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