title: Unprecedented Transformation of a Directing Group Generated In Situ and Its Application in the One-Pot Synthesis of 2-Alkenyl Benzonitriles.
abstract: An unprecedented protocol for the transformation of benzoyl azides into benzonitrile derivatives via iminophosphoranes generated in situ is described. The strategy was successfully applied to the de-novo synthesis of 2-alkenylated benzonitrile derivatives from benzoyl azides through ortho C-H activation/alkenylation followed by subsequent rearrangement. The salient features of this protocol involve incorporation of two important functionalities through cyanation and olefination in one pot under mild reaction conditions by using a less expensive Ru catalyst. The mechanism was established by isolating and characterising (using (31) P NMR) an intermediate with two ortho functionalities, iminophosphorane and olefin, under specific reaction conditions.
authors.affiliation: Medicinal & Process Chemistry Division, Institution CSIR-Central Drug Research Institute, Lucknow, 226031 (India), Tel.: (+91) 522-2612411-18, Fax: (+91) 522-2623405.|Academy of Scientific and Innovative Research, New Delhi, 110001 (India).
authors.forename: Ravi
authors.initials: R
authors.lastname: Kumar
authors.affiliation: Medicinal & Process Chemistry Division, Institution CSIR-Central Drug Research Institute, Lucknow, 226031 (India), Tel.: (+91) 522-2612411-18, Fax: (+91) 522-2623405.
authors.forename: Rajesh K
authors.initials: RK
authors.lastname: Arigela
authors.affiliation: Medicinal & Process Chemistry Division, Institution CSIR-Central Drug Research Institute, Lucknow, 226031 (India), Tel.: (+91) 522-2612411-18, Fax: (+91) 522-2623405. bijoy_kundu@yahoo.com.|Academy of Scientific and Innovative Research, New Delhi, 110001 (India). bijoy_kundu@yahoo.com.
authors.forename: Bijoy
authors.initials: B
authors.lastname: Kundu
keywords: CC coupling; CH activation; azides; olefination; rearrangement