γ-C—H-Functionalization of 4-octyne by the reactions with gallium 1,2-zwitterionic complexes of methylidenemalonates

γ-C—H-Functionalization of 4-octyne by the reactions with gallium 1,2-zwitterionic complexes of methylidenemalonates Full article

Journal

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Output data

Year: 2026, Volume: 75, Number: 4, Pages: 1107-1114 Pages count : 8 DOI: 10.1007/s11172-026-4962-x

Authors

Borisov D.D. ¹ , Novikov R.A. ¹ , Tomilov Yu.V. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

The reactions of the gallium 1,2-zwitterionic complexes of methylidenemalonates (generated from 2-arylcyclopropane-1,1-dicarboxylates and gallium halides, ratio 1: 1.2) with 4-octyne as a model internal alkyne proceed via several routes predetermined, to a significant extent, by reaction conditions. A poorly known mono-γ-C—H-functionalization of the alkyne residue occurs along with the known reactions at −20 °C in the presence of 2.5 equiv. GaCl3. The optimization of this process made it possible to develop an access to substituted hexahydrocyclopenta[a]naphthalenes in the yield up to 58%, and the role of a GaCl3 excess for this reaction route was shown.

Borisov D.D. , Novikov R.A. , Tomilov Y.V.
γ-C—H-Functionalization of 4-octyne by the reactions with gallium 1,2-zwitterionic complexes of methylidenemalonates
Russian Chemical Bulletin. 2026. V.75. N4. P.1107-1114. DOI: 10.1007/s11172-026-4962-x OpenAlex

Борисов Д.Д. , Новиков Р.А. , Томилов Ю.В.
γ-C—H-Функционализация 4-октина в реакциях с галлиевыми 1,2-цвиттер-ионными комплексами метилиденмалонатов
Известия Академии наук. Серия химическая. 2026. Т.75. №4. С.1107-1114.

Submitted:	Nov 10, 2025
Published online:	Jun 29, 2026

≡ OpenAlex:

W7166503350