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Copper‐Catalyzed Borylation of α‐Alkoxy Allenes with Bis(pinacolato)diboron: Efficient Synthesis of 2‐Boryl 1,3‐Butadienes
Author(s) -
Semba Kazuhiko,
Fujihara Tetsuaki,
Terao Jun,
Tsuji Yasushi
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.201306843
Subject(s) - borylation , chemistry , alkoxy group , catalysis , boranes , carbene , copper , allene , ligand (biochemistry) , medicinal chemistry , organic chemistry , boron , aryl , biochemistry , alkyl , receptor
Something solid to build on : 2‐Boryl 1,3‐butadienes with various substitution patterns were formed in good to high yields in a copper‐catalyzed borylation of α‐alkoxy allenes with bis(pinacolato)diboron (see scheme; Bn=benzyl, pin=pinacolate, L is an N‐heterocyclic carbene ligand). The products were found to be useful intermediates for the synthesis of cyclic vinyl boranes, α,β‐unsaturated ketones, and functionalized multisubstituted dienes.