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Rh(iii)-catalyzed regioselective intermolecular N-methylene Csp(3)–H bond carbenoid insertion
A Rh(iii)-catalyzed regioselective intermolecular carbenoid insertion into the N-methylene Csp(3)–H bond of acyclic aliphatic amides has been achieved, taking advantage of bidentate–chelation assistance. This methodology has been successfully applied to a broad range of linear and branched-chain N-a...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Royal Society of Chemistry
2017
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5874982/ https://www.ncbi.nlm.nih.gov/pubmed/29629165 http://dx.doi.org/10.1039/c7sc03802j |
Sumario: | A Rh(iii)-catalyzed regioselective intermolecular carbenoid insertion into the N-methylene Csp(3)–H bond of acyclic aliphatic amides has been achieved, taking advantage of bidentate–chelation assistance. This methodology has been successfully applied to a broad range of linear and branched-chain N-alkylamides, thus providing a practical method for the assembly of diverse beta-amino esters. Mechanism studies and density functional theory (DFT) calculations revealed that a singlet Fischer type carbene insertion via an outer-sphere pathway was involved in this N-methylene Csp(3)–H bond carbenoid insertion. |
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