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Direct Observation of Aldehyde Insertion into Rhodium−Aryl and −Alkoxide Complexes

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Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107
Cite this: J. Am. Chem. Soc. 2002, 124, 8, 1674–1679
Publication Date (Web):January 29, 2002
https://doi.org/10.1021/ja017401e
Copyright © 2002 American Chemical Society

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    Several organorhodium(I) complexes of the general formula (PPh3)2(CO)RhR (R = p-tolyl, o-tolyl, Me) were isolated and were shown to insert aryl aldehydes into the aryl−rhodium(I) bond. Under nonaqueous conditions, these reactions provided ketones in good yield. The stability of the arylrhodium(I) complexes allowed these reactions to be run also in mixtures of THF and water. In this solvent system, diarylmethanols were generated exclusively. Mechanistic studies support the formation of ketone and diarylmethanol by insertion of aldehyde into the rhodium−aryl bond and subsequent β-hydride elimination or hydrolysis to form diaryl ketone or diarylmethanol products. Kinetic isotope effects and the formation of diarylmethanols in THF/water mixtures are inconsistent with oxidative addition of the acyl carbon−hydrogen bond and reductive elimination to form ketone. Moreover, the intermediate rhodium diarylmethoxide formed from insertion of aldehyde was observed directly during the reaction. Its structure was confirmed by independent synthesis. This complex undergoes β-hydrogen elimination to form a ketone. This alkoxide also reacts with a second aldehyde to form esters by insertion and subsequent β-hydrogen elimination. Thus, reactions of arylrhodium complexes with an excess of aldehyde formed esters by a double insertion and β-hydrogen elimination sequence.

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