The application of a new set of diazo reagents to site-selective C–H functionalization is described. The 2,2,2-trichloroethyl aryldiazoacetates result in more robust and efficient carbenes relative to the corresponding methyl esters in rhodium-catalyzed reactions. Together with the catalyst Rh2(R-BPCP)4, a relatively new catalyst that is considered to have substantial steric bulk, these reagents are capable of enantioselective functionalization of methyl groups. In particular, the trichloroethyl aryldiazoacetates are capable of undergoing highly asymmetric C–H functionalization reactions with a range of methyl ethers, which had not been previously achieved. The efficiency of these reagents is demonstrated in the C–H functionalization reactions with some heteroaryldiazoacetates, in which considerably higher yields were observed relative to the corresponding diazo compounds with methyl esters.

2,2,2-Trichloroethyl aryldiazoacetates as robust reagents for site-selective C–H functionalization

249th National Meeting (2015)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.