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Synfacts 2025; 21(07): 710
DOI: 10.1055/a-2601-4104
Metals in Synthesis

Donor/Donor Rhodium Carbenes as Isobenzofuran Precursors

Contributor(s):
Mark Lautens 
,
Justin Ching
Morita N, Yoshikawa S, Ota E, Yamaguchi J *. Waseda University, Shinjuku, Japan
Rh-Catalyzed Synthesis of Isobenzofurans via Donor/Donor-Type Metal Carbenoids and Their [4 + 2] Cycloaddition.

J. Org. Chem. 2025;
90: 5986-5999
DOI: 10.1021/acs.joc.5c00339
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Keywords

rhodium catalysis - carbenes - cycloaddition

Significance

Yamaguchi and co-workers report the use of donor/donor diazo compounds as rhodium carbene precursors for the synthesis of isobenzofurans. These products were then subsequently subjected to a Diels–Alder reaction with either alkenes or alkynes to access substituted oxabicycles.


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Comment

The role of rhodium proved critical for this reaction. In the absence of rhodium, the decomposition of the diazo species would generate the resulting carbene, which preferentially underwent intermolecular cyclopropanation of the alkene rather than intramolecular cyclization to form the isobenzofurans.


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Publication History

Article published online:
23 June 2025

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