The concept of Gallium-controlled double C–H functionalization of aliphatic CH2-groups driven by Vinyl carbocations

Roman A. Novikov (), Denis D. Borisov, Dmitry A. Denisov, Maxim A. Novikov, Konstantin V. Potapov, Yaroslav V. Tkachev and Yury V. Tomilov
Additional contact information
Roman A. Novikov: Russian Academy of Sciences
Denis D. Borisov: Russian Academy of Sciences
Dmitry A. Denisov: Russian Academy of Sciences
Maxim A. Novikov: Russian Academy of Sciences
Konstantin V. Potapov: Russian Academy of Sciences
Yaroslav V. Tkachev: Russian Academy of Sciences
Yury V. Tomilov: Russian Academy of Sciences

Nature Communications, 2024, vol. 15, issue 1, 1-11

Abstract: Abstract The direct C–H activation of inert C(sp3)–H bonds in a hydrocarbon chain has been a very attractive target in organic synthesis for many decades. Among all the variety of processes, those driven by vinyl carbocations are quite scarce thus far, and it is hard to control for unstabilized vinyl cations. In this study, we designed a double C(sp3)–H functionalization of unactivated alkyl CH2 groups to produce a totally substituted quaternary carbon stereocenter via insertion of vinyl carbocations. These processes represent complicated reaction cascades with high molecular complexity controlled by the cooperative action of Ga(III) salts & GaHal4– anions and allow one-step deep poly-functionalization of simple CH substrates to be performed. In practice, this concept was initially implemented with simple starting compounds such as alkyl acetylenes and activated cyclopropanes, alkenes, or cyclobutanes to construct norbornane, cyclopentatetralin, and other important skeletons.

Date: 2024
References: View references in EconPapers View complete reference list from CitEc
Citations:

Downloads: (external link)
https://www.nature.com/articles/s41467-024-51237-5 Abstract (text/html)

Related works:
This item may be available elsewhere in EconPapers: Search for items with the same title.

Export reference: BibTeX RIS (EndNote, ProCite, RefMan) HTML/Text

Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-51237-5

Ordering information: This journal article can be ordered from
https://www.nature.com/ncomms/

DOI: 10.1038/s41467-024-51237-5

Access Statistics for this article

Nature Communications is currently edited by Nathalie Le Bot, Enda Bergin and Fiona Gillespie

More articles in Nature Communications from Nature
Bibliographic data for series maintained by Sonal Shukla () and Springer Nature Abstracting and Indexing ().