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Selective Metal‐free HB(C 6 F 5 ) 2 Catalyzed Allene Cyclotrimerization: Formation of 1,3,5‐Trimethylenecyclohexane and Its Tris‐hydroboration Product
Author(s) -
Tao Xin,
Kehr Gerald,
Daniliuc Constantin G.,
Erker Gerhard
Publication year - 2017
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.201610530
Subject(s) - allene , borane , hydroboration , chemistry , cyclohexane , catalysis , metal , tris , medicinal chemistry , stereochemistry , organic chemistry , biochemistry
Allene is cyclotrimerized under metal‐free conditions with the borane HB(C 6 F 5 ) 2 catalyst to selectively give 1,3,5‐trimethylenecyclohexane ( 3 a ). Three‐fold hydroboration of the 1,3,5‐cyclotrimer with Piers’ borane gives the all‐ cis 1,3,5‐CH 2 B(C 6 F 5 ) 2 substituted cyclohexane product 14 .