Carbon-catalysed reductive hydrogen atom transfer reactions

被引:92
作者
Yang, Huimin [1 ,2 ]
Cui, Xinjiang [1 ]
Dai, Xingchao [1 ,2 ]
Deng, Youquan [1 ]
Shi, Feng [1 ]
机构
[1] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Ctr Green Chem & Catalysis, Lanzhou 730000, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
基金
中国国家自然科学基金;
关键词
SELECTIVE TRANSFER HYDROGENATION; N-ALKYLATION; GRAPHITE OXIDE; GRAPHENE OXIDE; OXIDATIVE DEHYDROGENATION; MICHAEL ADDITION; PRIMARY AMINES; ALCOHOLS; EFFICIENT; SULFONAMIDES;
D O I
10.1038/ncomms7478
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
Generally, transition metal catalysts are essential for the reductive hydrogen atom transfer reaction, which is also known as the transfer hydrogenation reaction or the borrowing-hydrogen reaction. It has been reported that graphene can be an active catalyst in ethylene and nitrobenzene reductions, but no report has described carbon-based materials as catalysts for alcohol amination via the borrowing-hydrogen reaction mechanism. Here we show the results from the preparation, characterization and catalytic performance investigation of carbon catalysts in transition metal-free borrowing-hydrogen reactions using alcohol amination and nitro compound/ketone reduction as model reactions. XPS, XRD, SEM, FT-IR and N-2 adsorption-desorption studies revealed that C = O group in the carbon catalysts may be a possible catalytically active site, and high surface area is important for gaining high activity. The activity of the carbon catalyst remained unchanged after reuse. This study provides an attractive and useful methodology for a wider range of applications.
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页数:11
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共 69 条
[1]   Inverting the Diastereoselectivity of the Mukaiyama-Michael Addition with Graphite-Based Catalysts [J].
Acocella, Maria Rosaria ;
Mauro, Marco ;
Falivene, Laura ;
Cavallo, Luigi ;
Guerra, Gaetano .
ACS CATALYSIS, 2014, 4 (02) :492-496
[2]   Metal-catalysed approaches to amide bond formation [J].
Allen, C. Liana ;
Williams, Jonathan M. J. .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (07) :3405-3415
[3]   Nickel Nanoparticles in Hydrogen Transfer Reactions [J].
Alonso, Francisco ;
Riente, Paola ;
Yus, Miguel .
ACCOUNTS OF CHEMICAL RESEARCH, 2011, 44 (05) :379-391
[4]   The Catalytic Amination of Alcohols [J].
Baehn, Sebastian ;
Imm, Sebastian ;
Neubert, Lorenz ;
Zhang, Min ;
Neumann, Helfried ;
Beller, Matthias .
CHEMCATCHEM, 2011, 3 (12) :1853-1864
[5]   Graphene oxide as a carbocatalyst: the first example of a one-pot sequential dehydration-hydrothiolation of secondary aryl alcohols [J].
Basu, Basudeb ;
Kundu, Samir ;
Sengupta, Debasish .
RSC ADVANCES, 2013, 3 (44) :22130-22134
[6]   Different types of biological proton transfer reactions studied by quantum chemical methods [J].
Blomberg, Margareta R. A. ;
Siegbahn, Per E. M. .
BIOCHIMICA ET BIOPHYSICA ACTA-BIOENERGETICS, 2006, 1757 (08) :969-980
[7]   Use of Graphite Oxide and Graphene Oxide as Catalysts in the Synthesis of Dipyrromethane and Calix[4]pyrrole [J].
Chauhan, Shive Murat Singh ;
Mishra, Sweta .
MOLECULES, 2011, 16 (09) :7256-7266
[8]   Metal-free direct amidation of peptidyl thiol esters with α-amino acid esters [J].
Chen, Hao ;
He, Maomao ;
Wang, Yaya ;
Zhai, Linhui ;
Cui, Yongbo ;
Li, Yangyan ;
Li, Yan ;
Zhou, Haibing ;
Hong, Xuechuan ;
Deng, Zixin .
GREEN CHEMISTRY, 2011, 13 (10) :2723-2726
[9]   Molecular and textural engineering of conjugated carbon nitride catalysts for selective oxidation of alcohols with visible light [J].
Chen, Yan ;
Zhang, Jinshui ;
Zhang, Mingwen ;
Wang, Xinchen .
CHEMICAL SCIENCE, 2013, 4 (08) :3244-3248
[10]   Development of a General Non-Noble Metal Catalyst for the Benign Amination of Alcohols with Amines and Ammonia [J].
Cui, Xinjiang ;
Dai, Xingchao ;
Deng, Youquan ;
Shi, Feng .
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (11) :3665-3675