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J Am Chem Soc. 2016 Mar 2;138(8):2809-14. doi: 10.1021/jacs.5b13286. Epub 2016 Feb 18.

Surface-Controlled Mono/Diselective ortho C-H Bond Activation.

Author information

1
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 address ortho C-H functionalization and ortho-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, diselective ortho C-H bond activation on Au(111) surfaces and monoselective ortho 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 surface-assisted organic synthesis via the mono/diselective C-H bond activation.

PMID:
26853936
DOI:
10.1021/jacs.5b13286

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