Premium
Highly Selective Copper‐Catalyzed Hydroboration of Allenes and 1,3‐Dienes
Author(s) -
Semba Kazuhiko,
Shinomiya Masataka,
Fujihara Tetsuaki,
Terao Jun,
Tsuji Yasushi
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201300443
Subject(s) - hydroboration , chemistry , copper , protonation , catalysis , ligand (biochemistry) , diene , hydride , allene , combinatorial chemistry , organic chemistry , medicinal chemistry , metal , ion , biochemistry , natural rubber , receptor
The highly selective copper‐catalyzed hydroboration of allenes has been developed. Allylboranes and alkenylboranes were selectively prepared by the judicious choice of catalytic species (copper hydride and boryl copper). Furthermore, two types of alkenylboranes could be selectively synthesized by the choice of an appropriate ligand. Mechanistic studies confirmed that the protonation of a ( Z )‐σ‐allyl copper species, which was isolated and structurally characterized by single‐crystal X‐ray diffraction, was a key step in these reactions. Besides allenes, this method is also applicable to the selective hydroboration of 1,3‐diene derivatives to afford allylboranes and homoallylboranes.