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Addition of a Cyclophosphine to Nitriles: An Inorganic Click Reaction Featuring Protio, Organo, and Main‐Group Catalysis
Author(s) -
Chitnis Saurabh S.,
Sparkes Hazel A.,
Annibale Vincent T.,
Pridmore Natalie E.,
Oliver Alex M.,
Manners Ian
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.201704991
Subject(s) - heterolysis , cycloaddition , lone pair , chemistry , catalysis , yield (engineering) , group (periodic table) , click chemistry , functional group , combinatorial chemistry , medicinal chemistry , organic chemistry , molecule , materials science , metallurgy , polymer
The addition of a cyclotriphosphine to a broad range of nitriles gives access to the first examples of free 1‐aza‐2,3,4‐triphospholenes in a rapid, ambient temperature, one‐pot, high‐yield protocol. The reaction produces electron‐rich heterocycles (four lone pairs) and features homoatomic σ‐bond heterolysis, thereby combining the key features of the 1,3‐dipolar cycloaddition chemistry of azides and cyclopropanes. Also reported is the first catalytic addition of P−P bonds to the C≡N bond. The coordination chemistry of the new heterocycles is explored.