Efficient α-Alkylation of Arylacetonitriles with Secondary Alcohols Catalyzed by a Phosphine-Free Air-Stable Iridium(III) Complex

The Journal of Organic Chemistry
Surajit PandaBidraha Bagh

Abstract

A well-defined and readily available air-stable dimeric iridium(III) complex catalyzed α-alkylation of arylacetonitriles using secondary alcohols with the liberation of water as the only byproduct is reported. The α-alkylations were efficiently performed at 120 °C under solvent-free conditions with very low (0.1-0.01 mol %) catalyst loading. Various secondary alcohols including cyclic and acyclic alcohols and a wide variety of arylacetonitriles bearing different functional groups were converted into the corresponding α-alkylated products in good yields. Mechanistic study revealed that the reaction proceeds via alcohol activation by metal-ligand cooperation with the formation of reactive iridium-hydride species.

References

Jul 1, 1991·Journal of Medicinal Chemistry·S DeiF Gualtieri
Aug 4, 2005·Journal of the American Chemical Society·Jing ZhangDavid Milstein
Feb 1, 2006·Organic & Biomolecular Chemistry·Takao IkariyaRyoji Noyori
Mar 1, 2006·Chemical Society Reviews·Joseph S M SamecPeter Brandt
Jul 5, 2007·Chemical Communications : Chem Comm·Masao MoritaYasutaka Ishii
Aug 11, 2007·Science·Chidambaram GunanathanDavid Milstein
Oct 27, 2007·Accounts of Chemical Research·Takao Ikariya, A John Blacker
Dec 7, 2007·Chemical Communications : Chem Comm·Masato Ito, Takao Ikariya
Mar 24, 2009·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Takao Ikariya, Ilya D Gridnev
Dec 22, 2009·Dalton Transactions : an International Journal of Inorganic Chemistry·Hung Wai CheungChak Po Lau
May 21, 2010·Organic & Biomolecular Chemistry·Yan-Mei He, Qing-Hua Fan
Aug 7, 2010·Science·Andrew J A Watson, Jonathan M J Williams
Jul 8, 2011·Organic Letters·Bruno AnxionnatJanine Cossy
Jan 11, 2014·Inorganic Chemistry·Joaquín AlósMarta Valencia
Feb 9, 2017·Journal of the American Chemical Society·Wasim M AkhtarTimothy J Donohoe
Aug 10, 2017·Journal of the American Chemical Society·Subrata ChakrabortyDavid Milstein
Jul 26, 2018·Chemistry : a European Journal·Wei MaChao Wang
Nov 21, 2018·Angewandte Chemie·Jan SklyarukMagnus Rueping
Dec 12, 2018·Chemical Communications : Chem Comm·Antoine Bruneau-VoisineJean-Baptiste Sortais
Feb 23, 2019·Journal of the American Chemical Society·Subramanian Thiyagarajan, Chidambaram Gunanathan
May 23, 2019·The Journal of Organic Chemistry·Jannik C BorghsOsama El-Sepelgy
Jun 27, 2019·ChemSusChem·Priyanka ChakrabortyBasker Sundararaju

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