1‐Alkynyl(aryl)(tetrafluoroborato)‐λ 3 ‐bromanes as Highly Efficient Michael Acceptors: Uncatalyzed Conjugate Addition of 1‐Alkynyl(trialkyl)stannanes To Yield Symmetrical and Unsymmetrical 1,3‐Butadiynes | Zendy

Ochiai Masahito | Zendy; Nishi Yoshio | Zendy; Goto Satoru | Zendy; Frohn Hermann J. | Zendy

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1‐Alkynyl(aryl)(tetrafluoroborato)‐λ 3 ‐bromanes as Highly Efficient Michael Acceptors: Uncatalyzed Conjugate Addition of 1‐Alkynyl(trialkyl)stannanes To Yield Symmetrical and Unsymmetrical 1,3‐Butadiynes

Author(s) -

Ochiai Masahito,

Nishi Yoshio,

Goto Satoru,

Frohn Hermann J.

Publication year - 2005

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.200461985

Subject(s) - conjugate , aryl , chemistry , yield (engineering) , medicinal chemistry , oxidative coupling of methane , combinatorial chemistry , coupling reaction , catalysis , organic chemistry , materials science , mathematics , mathematical analysis , alkyl , metallurgy

Symmetrical 1,3‐diynes result from the oxidative homocoupling reaction of alkynylstannanes with an aryldifluoro‐λ 3 ‐bromane in the presence of BF 3 ⋅Et 2 O (see scheme, Ar= p ‐CF 3 C 6 H 4 ). The reaction involves a Michael addition of alkynylstannanes to the initially formed alkynyl‐λ 3 ‐bromanes. Cross‐coupling of alkynyl‐λ 3 ‐bromanes with alkynylstannanes affords unsymmetrical 1,3‐diynes (see scheme).

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