Unprecedented Reactivity of β‐Iodovinyl Sulfones: An Efficient Synthesis of β‐Keto Sulfones and β‐Keto Thiosulfones | Zendy

Reddy Raju Jannapu | Zendy; Kumar Jangam Jagadesh | Zendy; Kumari Arram Haritha | Zendy

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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.

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