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Dehydrogenative Homocoupling of Terminal Alkenes on Copper Surfaces: A Route to Dienes
Author(s) -
Sun Qiang,
Cai Liangliang,
Ding Yuanqi,
Xie Lei,
Zhang Chi,
Tan Qinggang,
Xu Wei
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201412307
Subject(s) - moiety , alkyl , aryl , scanning tunneling microscope , chemistry , density functional theory , copper , hydrocarbon , terminal (telecommunication) , diene , alkene , regioselectivity , functional group , surface modification , carbon fibers , nanotechnology , combinatorial chemistry , stereochemistry , organic chemistry , computational chemistry , materials science , composite number , catalysis , telecommunications , natural rubber , polymer , computer science , composite material
Homocouplings of hydrocarbon groups including alkynyl (sp 1 ), alkyl (sp 3 ), and aryl (sp 2 ) have recently been investigated on surfaces with the interest of fabricating novel carbon nanostructures/nanomaterials and getting fundamental understanding. Investigated herein is the on‐surface homocoupling of an alkenyl group which is the last elementary unit of hydrocarbons. Through real‐space direct visualization (scanning tunneling microscopy imaging) and density functional theory calculations, the two terminal alkenyl groups were found to couple into a diene moiety on copper surfaces, and is contrary to the common dimerization products of alkenes in solution. Furthermore, detailed DFT‐based transition‐state searches were performed to unravel this new reaction pathway.