CC Coupling with NO 2 /Alkyl Substitution at the Vinylic Carbon by Reaction of 2‐Aryl‐l‐nitro‐1‐alkenes with Dialkylzinc Compounds—A Novel Reaction | Zendy

Seebach Dieter | Zendy; Schäfer Harald | Zendy; Schmidt Beat | Zendy; Schreiber Martin | Zendy

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CC Coupling with NO 2 /Alkyl Substitution at the Vinylic Carbon by Reaction of 2‐Aryl‐l‐nitro‐1‐alkenes with Dialkylzinc Compounds—A Novel Reaction

Author(s) -

Seebach Dieter,

Schäfer Harald,

Schmidt Beat,

Schreiber Martin

Publication year - 1992

Publication title -

angewandte chemie international edition in english

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 0570-0833

DOI - 10.1002/anie.199215871

Subject(s) - aryl , alkyl , nitro , chemistry , coupling reaction , medicinal chemistry , catalysis , substitution reaction , organic chemistry

No catalyst is needed for the novel vinylic CC coupling reaction of 2‐aryl‐1‐nitroalkenes with dialkylzinc compounds [Eq. (a)]. Although NO 2 substituents usually activate double bonds for Michael additions, replacement of the NO 2 group with an alkyl group provides ( E )‐1‐aryl‐ and ( E ) ‐1‐heteroaryl‐1‐alkenes in yields up to 40%, which can probably still be optimized.

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