B(C₆F₅)₃-Catalyzed Direct Deoxygenative Alkenylation of Ketones with Pinacolborane.

Authors

Wenwen Chen, Wenjie Zheng, Moke Xu, Qian Jin, Jianing Yang, Yuanling Hu, Rong Jiang, Yinlin Shao, Fangjun Zhang

Published in

The Journal of organic chemistry. Oct 23, 2025. Epub Oct 23, 2025.

Abstract

This investigation presents an innovative methodology for the direct deoxygenative alkenylation of ketones, utilizing pinacolborane as the reducing agent in the presence of the B(C₆F₅)₃ catalyst. A series of aryl ketones containing different functional groups such as hydroxyl, amino, alkynyl, vinyl, and ester groups were found to be well-tolerated. The efficiency of deoxygenative alkenylation could be notably improved by the addition of catalytic LuCl₃ in some substrates. This transformation has also been nicely applied to the gram-scale late-stage functionalization of pharmacologically significant compounds sertraline and conivaptan. Comprehensive mechanistic investigations have elucidated a plausible reaction pathway that proceeds through sequential carbonyl hydroboration, deboration, and deprotonation processes.

PMID:
41129740
Bibliographic data and abstract were imported from PubMed on 24 Oct 2025.

Read full publication at:
Please sign in to see all details.

Stats

1-terrible, 9-excellent. How would you rate this publication? Sign in in to submit your rating.

Post a comment

You need to be signed in to post comments. You can sign in here.

Comments

There are no comments yet.