Activation of Remote meta‐C−H Bonds in Arenes with Tethered Alcohols: A Salicylonitrile Template. Issue 40 (23rd August 2017)

• Record Type: Journal Article
• Authors: Zhang, Lanlan; Zhao, Chaoyue; Liu, Yang; Xu, Jiancong; Xu, Xiufang; Jin, Zhong
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 40(2017)
• Page Start: 12245
• Page End: 12249
• Publication Date: 2017-08-23
• Subjects: arenes -- C−H activation -- density-functional calculations -- palladium -- regioselectivity; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201705495
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: Palladium‐catalyzed activation of remote meta ‐C−H bonds in arenes containing tethered alcohols was achieved with high regioselectivity by using a nitrile template. Computational studies on the macrocyclic transition state of the regioselectivity‐determining C−H activation steps revealed that both the C‐N‐Ag angles and gauche comformations of phenyl ether play an extremely important role in the meta selectivity. Abstract : From a distance : Palladium‐catalyzed activation of remote C−H bonds arenes containing long‐chain alcohols is achieved with high meta regioselectivity by using a salicylonitrile template. DFT calculations show that the regioselectivity of products greatly depends on both the C‐N‐Ag angle and gauche comformation of phenyl ether in the macrocyclic transition state.