Organic Chemistry Portal

Abstracts

Search:

TBAT-Catalyzed Deoxygenative Reduction of Tertiary Amides to Amines

Vinothkumar Vinayagam*, Subir Kumar Sadhukhan, Satish Kumar Karre, Ravuri Srinath, Ravi Kumar Maroju, Purushotham Reddy Karra, Hema Sundar Naveen Babu Bathula, Siva Kundrapu and Srikanth Reddy Surukonti

*Medicinal Chemistry Division, Curia India Pvt. Ltd, MN park, Genome Valley, Turkapally 500078, Hyderabad, India, Email: VinothKumar.Vinayagamcuriaglobal.com

V. Vineyagam, S. K. Sadhukhan, S. K. Karre, R. Srinath, R. K. Maroju, P. R. Karra, H. S. N. B. Bathula, S. Kundrapu, S. R. Surukonti, Org. Lett., 2023, 25, 4610-4614.

DOI: 10.1021/acs.orglett.3c01150


see article for more reactions

Abstract

A simple, mild, metal-free catalytic protocol for an efficient conversion of amides to amines at r.t. uses the stable tetrabutylammonium difluorotriphenylsilicate in combination with silanes that generates a highly reactive hydrosilicate species. The attractive features of this protocol include operational simplicity, safety, broad substrate scope, good yields, and amenable to scale up.

see article for more examples


proposed mechanism



Key Words

reduction of amides, phenylsilane


ID: J54-Y2023