Rh(III)-catalysed C-H annulation of cis -stilbene acids with 2-diazo-1,3-diketones: facile access to 6,7-dihydrobenzofuran-4(5 H )-one and α-pyrone scaffolds

An efficient Rh(III)-catalysed C-H functionalization, tandem annulation of -stilbene acids using 2-diazo-1,3-diketones was devised. This protocol solely afforded 6,7-dihydrobenzofuran-4(5 )-ones using alicyclic diazocarbonyls decarbonylation and α-pyrones with aliphatic diazo compounds. The chameleo...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2024-05, Vol.22 (19), p.3933-3939
Main Authors: Galla, Mary Sravani, Kale, Nandini B, Kumawat, Akshay, Bora, Darshana, Shankaraiah, Nagula
Format: Article
Language:English
Subjects:
Atom economy
Carboxylic acids
Chemical reactions
Diketones
Functional groups
Organic chemistry
Stilbene
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Summary:An efficient Rh(III)-catalysed C-H functionalization, tandem annulation of -stilbene acids using 2-diazo-1,3-diketones was devised. This protocol solely afforded 6,7-dihydrobenzofuran-4(5 )-ones using alicyclic diazocarbonyls decarbonylation and α-pyrones with aliphatic diazo compounds. The chameleonic nature of -stilbene acid was observed with various diazo compounds by altering the additives. This synthetic method furnished good atom-economy and wide functional group tolerance, and also explained the use of carboxylic acids as a directing group. In addition, a mechanistic investigation of the catalysed reaction using ESI-MS, and the fluorescence properties of α-pyrones were well explored.
ISSN:1477-0520
1477-0539
DOI:10.1039/d4ob00151f