Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 30, Pages 10353-10360Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201904608
Keywords
allylic compounds; C-H activation; olefins; palladium; reaction mechanisms
Categories
Funding
- SERB-India [CRG/2018/003951]
- SERB-NPDF [PDF/2016/002187]
- A*STAR Singapore
- EPSRC Centre for Doctoral Training in Theory and Modelling in Chemical Sciences [EP/L015722/1]
Ask authors/readers for more resources
Palladium(II)-catalyzed meta-selective C-H allylation of arenes has been developed utilizing synthetically inert unactivated acyclic internal olefins as allylic surrogates. The strong sigma-donating and pi-accepting ability of pyrimidine-based directing group facilitates the olefin insertion by overcoming inertness of the typical unactivated internal olefins. Exclusive allyl over styrenyl product selectivity as well as E stereoselectivity were achieved with broad substrate scope, wide functional-group tolerance, and good to excellent yields. Late-stage functionalisations of pharmaceuticals were demonstrated. Experimental and computational studies shed light on the mechanism and point to key steric control in the palladacycle, thus determining product selectivities.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available