Journal
ACS CATALYSIS
Volume 6, Issue 2, Pages 969-973Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.5b02532
Keywords
C-C activation; isocyanate; isatin; cycloaddition; rhodium
Categories
Funding
- CPRIT
- NIGMS [R01GM109054]
- Welch Foundation [F 1781]
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The first decarbonylative cycloaddition of less-strained cyclic ketones (isatins) with isocyanates is reported. Initiated by C-C activation, this distinct [5 - 2 + 2] transformation provides a rapid entry to access various benzimidazolidinone derivatives, and a wide range of isocyanates can be efficiently coupled with broad functional group tolerance. A modified one-pot process combining a Curtius rearrangement and C-C activation was also achieved by using acyl azides as the starting materials. A detailed mechanistic study revealed a surprising double-decarbonylative reaction pathway. The novel reactivity discovered in this basic research is expected to shed light on the development of new heterocycle formation methods through C-C/isocyanate coupling.
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