Ru(II)-Catalyzed C-H Activation: Amide-Directed 1,4-Addition of the Ortho C-H Bond to Maleimides.

Autor: Keshri P; Department of Organic Chemistry, Indian Institute of Science , Bangalore, Karnataka 560 012, India., Bettadapur KR; Department of Organic Chemistry, Indian Institute of Science , Bangalore, Karnataka 560 012, India., Lanke V; Department of Organic Chemistry, Indian Institute of Science , Bangalore, Karnataka 560 012, India., Prabhu KR; Department of Organic Chemistry, Indian Institute of Science , Bangalore, Karnataka 560 012, India.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2016 Jul 15; Vol. 81 (14), pp. 6056-65. Date of Electronic Publication: 2016 Jul 07.
DOI: 10.1021/acs.joc.6b01160
Abstrakt: Maleimide has been used as a selective coupling partner to generate conjugate addition products exclusively. The typical Heck-type oxidative coupling that occurs when alkenes are used is avoided by choosing maleimide as an alkene, which cannot undergo β-hydride elimination due to the unavailability of a syn-periplanar β-hydrogen atom. The amide nitrogen, which is notorious for undergoing tandem reactions to generate spirocyclic or annulation products under cross-coupling conditions, remains innocent in this report. Along with the substrate scope, a robustness screen has been performed to analyze the performance of amide as a directing group in the presence of other directing groups and also to examine the tolerance of the reaction conditions for other frequently encountered functional groups.
Databáze: MEDLINE