Rhodium-Catalyzed Isomerization of α-Arylpropargyl Alcohols to Indanones: Involvement of an Unexpected Reaction Cascade
- 11 February 2005
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 127 (9), 2872-2873
- https://doi.org/10.1021/ja042582g
Abstract
A rhodium-catalyzed isomerization of α-arylpropargyl alcohols to indanones has been developed under mild conditions. Considering the ease of preparation of these propargyl alcohols (terminal alkynes + aromatic aldehydes), this method provides a new way of constructing indanones with high efficiency. By the mechanistic investigations using deuterium-labeled substrates, it has also been demonstrated that the reaction goes through an unexpected cascade, with a 1,4-hydrogen shift being the turnover-limiting step of the catalytic cycle.This publication has 6 references indexed in Scilit:
- Catalytic Cycle of Rhodium-Catalyzed Asymmetric 1,4-Addition of Organoboronic Acids. Arylrhodium, Oxa-π-allylrhodium, and Hydroxorhodium IntermediatesJournal of the American Chemical Society, 2002
- Intermolecular C−H Activation of Hydrocarbons by Tungsten Alkylidene Complexes: An Experimental and Computational Mechanistic StudyOrganometallics, 2001
- Rhodium-Catalyzed Hydroarylation of Alkynes with Arylboronic Acids: 1,4-Shift of Rhodium from 2-Aryl-1-alkenylrhodium to 2-Alkenylarylrhodium IntermediateJournal of the American Chemical Society, 2001
- Two-metal catalyst system for redox isomerization of propargyl alcohols to enals and enones.Journal of the American Chemical Society, 1995
- A Simple and Convenient Preparation of [(Ph3P)4Rh2(.mu.-OH)2] and Its Reactions with C-H, O-H, and M-H AcidsOrganometallics, 1995
- Rhodium-catalysed redox isomerization of hydroxy alkynes to trans keto and hydroxy vinyl esters. A short and stereoselective synthesis of dipeptide isostersTetrahedron Letters, 1995