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 Научная публикация

Журнал

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

Вых. Данные

Год: 2026, Том: 75, Номер: 4, Страницы: 1107-1114 Страниц : 8 DOI: 10.1007/s11172-026-4962-x

Авторы

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

Организации

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.

Поступила в редакцию:	10 нояб. 2025 г.
Опубликована online:	29 июн. 2026 г.

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