GaCl3-promoted C–H functionalization of ethylidenemalonate in reactions with internal alkynes

GaCl3-promoted C–H functionalization of ethylidenemalonate in reactions with internal alkynes Full article

Journal

Organic & Biomolecular Chemistry
ISSN: 1477-0520 , E-ISSN: 1477-0539

Output data

Year: 2026, DOI: 10.1039/d6ob00875e

Authors

Borisov Denis D. ¹ , Borisova Irina A. ¹ , Antanyazov Mikhail R. ^1,2 , Prolomov Ilya V. ¹ , Medvedev Michael G. ¹ , Novikov Roman A. ¹ , Tomilov Yury V. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation
2	Lomonosov Moscow State University, Leninskie Gory 1/3, 119991 Moscow, Russian Federation

The unprecedented C(sp2)–H functionalization of ethylidenemalonate with internal alkynes was discovered, leading to substituted vinylcyclopentanes as trans,trans-isomers (dr > 15 : 1). The experiment with deuterated ethylidenemalonate showed that the formation of substituted vinylcyclopentane is accompanied by a 1,2-hydride shift and mono-γ-C–H insertion into the internal alkyne.

Borisov D.D. , Borisova I.A. , Antanyazov M.R. , Prolomov I.V. , Medvedev M.G. , Novikov R.A. , Tomilov Y.V.
GaCl3-promoted C–H functionalization of ethylidenemalonate in reactions with internal alkynes
Organic & Biomolecular Chemistry. 2026. DOI: 10.1039/d6ob00875e WOS Scopus OpenAlex

Submitted:	Jun 5, 2026
Accepted:	Jul 31, 2026
Published online:	Sep 4, 2026

≡ Web of science:	WOS:001869655800001
≡ Scopus:	2-s2.0-105049675621
≡ OpenAlex:	W7208766654