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Unprecedented Reactivity of β‐Iodovinyl Sulfones: An Efficient Synthesis of β‐Keto Sulfones and β‐Keto Thiosulfones
Author(s) -
Reddy Raju Jannapu,
Kumar Jangam Jagadesh,
Kumari Arram Haritha
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900676
Subject(s) - chemistry , reactivity (psychology) , yield (engineering) , combinatorial chemistry , oxidative phosphorylation , biochemistry , materials science , medicine , alternative medicine , pathology , metallurgy
An unprecedented reactivity of ( E )‐β‐iodovinyl sulfones in the presence of NaOAc is reported. The ( E )‐β‐iodovinyl sulfones were treated with NaOAc in DMSO/H 2 O to yield β‐keto sulfones in moderate to high yields. A novel oxidative difunctionalization of β‐iodovinyl sulfones with thiosulfonates and NaOAc in DMF has been developed. This metal‐free oxosulfenylation is an operationally simple to access a wide range of β‐keto thiosulfones (α‐thioaryl‐β‐keto sulfones) in moderate to high yields. The transformations were reliable at gram‐scale, thus illustrating its efficiency and practicality. A plausible mechanism for the protocol is also proposed.