Hydrocyanative Cyclization and Three‐Component Cross‐Coupling Reaction between Allenes and Alkynes under Nickel Catalysis | Zendy

Arai Shigeru | Zendy; Amako Yuka | Zendy; Yang Xiaofei | Zendy; Nishida Atsushi | Zendy

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Hydrocyanative Cyclization and Three‐Component Cross‐Coupling Reaction between Allenes and Alkynes under Nickel Catalysis

Author(s) -

Arai Shigeru,

Amako Yuka,

Yang Xiaofei,

Nishida Atsushi

Publication year - 2013

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201303883

Subject(s) - regioselectivity , alkyne , chemistry , stereoselectivity , catalysis , coupling reaction , acetone , nickel , medicinal chemistry , organic chemistry , combinatorial chemistry

Packed with functionality : The key step in the title reactions with acetone cyanohydrin is a regioselective hydronickelation of allenes. Subsequent carbometalation of the alkyne followed by reductive elimination gave cyano‐functionalized tetrasubstituted alkenes in a regio‐ and stereoselective manner (see scheme; EWG=electron‐withdrawing group, Ts= p ‐toluenesulfonyl).

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