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Synfacts 2015; 11(1): 0051
DOI: 10.1055/s-0034-1379688
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Divergent Reactivity of 2-Triazole Benzaldehydes under Rhodium Catalysis

Contributor(s):
Mark Lautens
,
Thomas Johnson
Shen H, Fu J, Gong J, * Yang Z. * Peking University, Beijing and Ocean University of China, Qingdao, P. R. of China
Tunable and Chemoselective Syntheses of Dihydroisobenzofurans and Indanones via Rhodium-Catalyzed Tandem Reactions of 2-Triazole-benzaldehydes and 2-Triazole-alkylaryl Ketones.

Org. Lett. 2014;
16: 5588-5591
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Publication History

Publication Date:
15 December 2014 (online)

 
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Key words

triazoles - rhodium - carbenoids - indanones

Significance

N-Sulfonyl 1,2,3-triazoles can serve as convenient diazo compound precursors, when reacted with a suitable rhodium(II) catalyst. In the present report, the authors present the reaction of 2-triazole benzaldehydes and 2-triazole alkylaryl ketones with water and alcohols. The products generated are either valuable 2-amino-3-hydroxylindanones or dihydroisobenzofurans.


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Comment

To support the existence of an oxonium intermediate, the starting triazole was reacted with the rhodium catalyst for two hours in the absence of nucleophiles. Upon addition of water, alcohol and Sc(OTf)3, products arising from paths A and B were formed in comparable yield, suggesting the presence of this common intermediate.


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