Highly Diastereoselective Radical Cyclopropanation of Olefins via Cobaloxime‐Based Metalloradical Catalysis DOI Open Access
Liming Tan, McKay Boehme,

Lorenzo Papworth

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 7, 2024

Abstract Metalloradical catalysis (MRC), predominantly exemplified by metalloporphyrin complexes, has emerged as a promising strategy for regulating radical reactions and broadening their synthetic applications. In this paper, we report that cobaloxime functioning surrogate systems, can mediate cyclopropanation of olefins using donor/acceptor‐type carbene precursor α‐aryl diazoacetates through the MRC process. The reaction proceeds under mild conditions, yielding cyclopropane derivatives in good yields with high diastereoselectivity. exhibits extensive substrate tolerance, encompassing gram‐scale transformations synthesis pharmaceutical compounds. Our discoveries underscore potential cobaloxime‐catalyzed valuable asset organic syntheses further expand repertoire metalloradical systems catalysis.

Language: Английский

Copper-catalyzed C–N cross-coupling for construction of alkylated N-cyanamide derivatives via nitrogen umpolung DOI
Yanjun Wan,

Harriet K. Zhang,

Jin Qian

et al.

Chem, Journal Year: 2024, Volume and Issue: 10(8), P. 2538 - 2549

Published: May 21, 2024

Language: Английский

Citations

2
Visible‐Light‐Driven Formyl Group Migration Triggered Remote Desaturation DOI

Yuwei Hong,

Yizhou Qin,

Xiong Yang

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(28)

Published: May 10, 2024

Abstract Dehydrogenation of unactivated alkanes to form versatile alkenes is an important but challenging task in synthetic chemistry. Enabled by a radical‐mediated formyl group migration, novel visible light‐induced remote desaturation aldehydes developed, delivering panel trifluoromethylated δ,ϵ‐ or γ,δ‐unsaturated moderate excellent yields with good functional tolerance at room temperature. Mechanistic studies indicate reaction pathway comprising the cascade trifluoromethylation C−C double bonds, intramolecular addition aldehydes, β‐fragmentation alkoxy radicals, single electron transfer oxidation, and deprotonation. It provides complementary approach existing protocols.

Language: Английский

Citations

0
Highly Diastereoselective Radical Cyclopropanation of Olefins via Cobaloxime‐Based Metalloradical Catalysis DOI Open Access
Liming Tan, McKay Boehme,

Lorenzo Papworth

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 7, 2024

Abstract Metalloradical catalysis (MRC), predominantly exemplified by metalloporphyrin complexes, has emerged as a promising strategy for regulating radical reactions and broadening their synthetic applications. In this paper, we report that cobaloxime functioning surrogate systems, can mediate cyclopropanation of olefins using donor/acceptor‐type carbene precursor α‐aryl diazoacetates through the MRC process. The reaction proceeds under mild conditions, yielding cyclopropane derivatives in good yields with high diastereoselectivity. exhibits extensive substrate tolerance, encompassing gram‐scale transformations synthesis pharmaceutical compounds. Our discoveries underscore potential cobaloxime‐catalyzed valuable asset organic syntheses further expand repertoire metalloradical systems catalysis.

Language: Английский

Citations

0