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 alpha-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.Keywords
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