Detailed Information

Chemoselective α-Alkylation and α-Olefination of Arylacetonitriles with Alcohols via Iron-Catalyzed Borrowing Hydrogen and Dehydrogenative Coupling : Chemoselective alpha-Alkylation and alpha-Olefination of Arylacetonitriles with Alcohols via Iron-Catalyzed Borrowing Hydrogen and Dehydrogenative Coupling

Cited 10 time in Web of Science Cited 13 time in Scopus

Putta, Ramachandra Reddy; Chun, Simin; Lee, Seok Beom; Hong, Junhwa; Choi, Seung Hyun; Oh, Dong-Chan; Hong, Suckchang

Issue Date
American Chemical Society
Journal of Organic Chemistry, Vol.87 No.24, pp.16378-16389
alpha-Alkyl and alpha-olefin nitriles are very important for organic synthesis and medicinal chemistry. However, different types of catalysts are employed to achieve either alpha-alkylation of nitriles by borrowing hydrogen or alpha-olefination by dehydrogenative coupling methods. Designing and developing high-performance earth-abundant catalysts that can procure different products from the same starting materials remain a great challenge. Herein, we report an iron(0) catalyst system that achieves chemoselectivity between borrowing hydrogen and dehydrogenative coupling protocols by simply changing the base. A broad range of nitriles and alcohols, including benzylic, linear aliphatic, cycloaliphatic, heterocyclic, and allylic alcohols, were selectively and efficiently converted to the corresponding products. Mechanistic studies reveal that the reaction mechanism proceeds through a dehydrogenative pathway. This iron catalytic protocol is environmentally benign and atom-efficient with the liberation of H2 and H2O as green byproducts.
Files in This Item:
There are no files associated with this item.
Appears in Collections:

Related Researcher

  • College of Pharmacy
  • Department of Manufacturing Pharmacy
Research Area Development of methodologies using metal catalyst, Total synthesis of natural products


Item View & Download Count

  • mendeley

Items in S-Space are protected by copyright, with all rights reserved, unless otherwise indicated.