Iodine(III)-Mediated Trifluoroacetylation of a C(sp 2 )-H or C(sp)-H Bond with Masked Trifluoroacyl Reagents.

Autor: Ye ZP; College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China., Guo M; College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China., Ye YQ; College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China., Yuan CP; College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China., Wang HL; College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China., Yang JS; College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China., Chen HB; College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China.; Jiangxi Time Chemical Company, Ltd., Fuzhou 344800, P. R. China., Xiang HY; College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China., Chen K; College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China.; Xiangjiang Laboratory, Changsha 410205, P. R. China., Yang H; College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China.; Xiangjiang Laboratory, Changsha 410205, P. R. China.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2024 Jun 21; Vol. 26 (24), pp. 5196-5201. Date of Electronic Publication: 2024 Jun 10.
DOI: 10.1021/acs.orglett.4c01780
Abstrakt: A novel strategy for incorporating a trifluoroacetyl functionality into a range of structurally varied unsaturated bonds was developed by using PhI(OCOMe) 2 as an oxidant with a masked trifluoroacyl reagent as a trifluoroacetyl radical precursor. The oxidative decarboxylation of the masked trifluoroacyl precursor followed by a tandem radical process provides versatile access to 5- exo - trig cyclization of N -arylacrylamides, direct C(sp 2 )-H trifluoroacetylation of quinolines, isoquinoline, 2 H -indazole, and quinoxalin-2(1 H )-ones, and C(sp)-H trifluoroacetylation of alkynes. This protocol is characterized by mild reaction conditions, operational simplicity, and broad functional group compatibility.
Databáze: MEDLINE