J. Am. Chem. Soc.: Surface-Controlled Mono/Diselectiveortho C−H Bond Activation

Title:

Surface-Controlled Mono/Diselectiveortho C−H Bond Activation

Authors:

Qing Li, Biao Yang, Haiping Lin, Nabi Aghdassi, Kangjian Miao, Junjie Zhang, Haiming Zhang, Youyong Li, Steffen Duhm, Jian Fan,* and Lifeng Chi*

Institution:

Institute of Functional Nano & Soft Materials (FUNSOM), Jiangsu Key Laboratory for Carbon-Based Functional Materials & Devices, Soochow University, 199 Ren’ai Road, Suzhou, 215123, Jiangsu, P. R. China

Abstract:

One of the most charming and challenging topics in organic chemistry is the selective C−H bond activation. The difficulty arises not only from the relatively large bond-dissociation enthalpy, but also from the poor reaction selectivity. In this work, Au(111) and Ag(111) surfaces were used to addressortho C−H functionalization andortho-ortho couplings of phenol derivatives. More importantly, the competition between dehydrogenation and deoxygenation drove the diversity of reaction pathways of phenols on surfaces, that is, diselectiveortho C−H bond activation on Au(111) surfaces and monoselectiveortho C−H bond activation on Ag(111) surfaces. The mechanism of this unprecedented phenomenon was extensively explored by scanning tunneling microscopy, density function theory, and X-ray photoelectron spectroscopy. Our findings provide new pathways for surfaceassisted organic synthesis via the mono/diselective C−H bond activation.

IF:

12.113

Link:

http://pubs.acs.org/doi/abs/10.1021/jacs.5b13286