Anti-Markovnikov hydroallylation reaction of alkenes via scandium-catalyzed allylic C‒H activation

Shiyu Wang, Lichao Ning, Tao Mao, Yuqiao Zhou, Maoping Pu, Xiaoming Feng and Shunxi Dong ()
Additional contact information
Shiyu Wang: College of Chemistry Sichuan University
Lichao Ning: College of Chemistry Sichuan University
Tao Mao: College of Chemistry Sichuan University
Yuqiao Zhou: College of Chemistry Sichuan University
Maoping Pu: College of Chemistry Sichuan University
Xiaoming Feng: College of Chemistry Sichuan University
Shunxi Dong: College of Chemistry Sichuan University

Nature Communications, 2025, vol. 16, issue 1, 1-11

Abstract: Abstract Compared with rare-earth (RE)…heteroatom interaction, RE…π interaction, frequently used in facilitating regio- and stereoselectivity of olefin polymerizations, is seldomly used to trigger catalytic C − H functionalization. Here, we describe a direct anti-Markovnikov hydroallylation reaction of styrene derivatives with 1-aryl-2-alkyl alkenes and α-alkenes by use of RE…π interaction. This protocol provides a straightforward and atom-efficient route for the synthesis of valuable chain elongated internal alkenes (65 examples, up to 99% yield, > 19:1 E/Z ratio). The reaction proceeds via an allylic Csp3‒H activation pathway initiated by site-selective deprotonation with the assistance of cationic imidazolin-2-iminato scandium alkyl species followed by alkene insertion into the resulting scandium-allyl bond. A catalytic amount of Lewis base additives, such as amine and tetrahydrofuran (THF) show significant effects on the reactivity and E/Z selectivity. The reaction mechanism is elucidated by experimental studies and theoretical calculations.

Date: 2025
References: View complete reference list from CitEc
Citations:

Downloads: (external link)
https://www.nature.com/articles/s41467-025-56602-6 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:16:y:2025:i:1:d:10.1038_s41467-025-56602-6

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

DOI: 10.1038/s41467-025-56602-6

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 ().