Journal
CHEMICAL SCIENCE
Volume 7, Issue 1, Pages 240-245Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5sc03110a
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Funding
- Ministry of Education, Culture, Sports, Science and Technology
- JST Strategic Basic Research Programs Advanced Catalytic Transformation Program for Carbon Utilization (ACT-C) from Japan Science and Technology Agency
- Grants-in-Aid for Scientific Research [14J00043, 15H02177] Funding Source: KAKEN
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An unprecedented C-H alkylation using alpha,beta-unsaturated gamma-lactones (butenolides) and dihydrofurans was achieved by the Rh-catalyzed reaction of benzamides. C-C bond formation occurs between the ortho-position of the benzamide derivative and the gamma-position of the butenolide or the a-position of the dihydrofuran. The presence of an 8-aminoquinoline directing group is crucial for the success of the reaction. The results of deuterium labeling experiments indicate that the cleavage of the C-H bond is reversible and suggest that a migratory carbene insertion is involved as the key step.
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