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Synthesis of Annelated Phospholes through Intramolecular CH Activation by Monovalent Phosphorus
Author(s) -
Wei Xinda,
Lu Zongming,
Zhao Xu,
Duan Zheng,
Mathey Francois
Publication year - 2015
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.201410603
Subject(s) - phosphinidene , intramolecular force , vicinal , chemistry , electrophile , phosphorus , biphenyl , medicinal chemistry , stereochemistry , organic chemistry , catalysis
Electrophilic terminal phosphinidene complexes [Ar‐Ar‐P‐W(CO) 5 ] (Ar‐Ar: biaryl or an analogue thereof) undergo a spontaneous insertion of the phosphorus atom into the vicinal CH bonds to give annelated phospholes. Twelve examples are described, including biphenyl, thienyl, pyrrolyl, and benzofuryl groups as biaryl moieties. The activation energy of the insertion reaction is quite low (about 2 kcal mol −1 ).