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Highly Selective Manganese(I)/Lewis Acid Cocatalyzed Direct C−H Propargylation Using Bromoallenes
Author(s) -
Zhu Can,
Schwarz Jonas Luca,
Cembellín Sara,
Greßies Steffen,
Glorius Frank
Publication year - 2018
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.201710835
Subject(s) - allene , manganese , selectivity , lewis acids and bases , reactivity (psychology) , chirality (physics) , catalysis , chemistry , transition metal , combinatorial chemistry , medicinal chemistry , organic chemistry , physics , medicine , chiral symmetry breaking , alternative medicine , pathology , quantum mechanics , nambu–jona lasinio model , quark
A manganese(I)/Lewis acid cocatalyzed direct C−H propargylation with high selectivity has been developed. BPh 3 was discovered to not only promote the reactivity, but also enhance the selectivity. Secondary, tertiary, and even quaternary carbon centers at the propargylic position could be directly constructed. Both internal and terminal alkynes are easily accessible. The chirality was successfully transferred from an axially chiral allene to central chirality. The reactivity of the manganese catalyst in this reaction was found to be unique among transition metal catalysts.