Unprecedented Transformation of a Directing Group Generated In Situ and Its Application in the One‐Pot Synthesis of 2‐Alkenyl Benzonitriles |
| |
Authors: | Ravi Kumar Rajesh K. Arigela Dr. Bijoy Kundu |
| |
Affiliation: | 1. Medicinal & Process Chemistry Division, Institution CSIR‐Central Drug Research Institute, Lucknow, 226031 (India), Tel.: (+91)?522‐2612411‐18, Fax: (+91)?522‐2623405;2. Academy of Scientific and Innovative Research, New Delhi, 110001 (India) |
| |
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 31P NMR) an intermediate with two ortho functionalities, iminophosphorane and olefin, under specific reaction conditions. |
| |
Keywords: | azides C C coupling C H activation olefination rearrangement |
|
|