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《Chinese Science Bulletin》 2015-31
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Recent progress on nickel-catalyzed direct functionalization of unactivated C–H bonds

ZHAN BeiBei;LIU Bin;HU Fang;SHI BingFeng;Department of Chemistry,Zhejiang University;  
Over the past few decades, transition-metal catalyzed direct functionalization of unactivated C–H bonds has emerged as an efficient and straightforward strategy for the construction of C–C and C–heteroatom bonds. It provides access to complex molecules via the direct cleavage of C–H bonds without the need of prefunctionalization, rendering this strategy more step-economical and environmentally benign. Recently, tremendous attentions have been devoted to the use of first row-transition metals as most of those metals are naturally abundant, readily available, and inexpensive and have low toxicities in comparison with precious metals. In addition, the exploration of new catalytic systems might lead to the discovery of new mode of reactions. The aim of this review is to give an overview on recent advances in nickel-catalyzed direct functionalization of unactivated C–H bonds, without the discussion of the cleavage of acidic C–H bonds. Firstly, nickel-catalyzed functionalization of C(sp2)–H to form new C–C and C–heteroatom bonds is reviewed. Secondly, an overview of Ni-catalyzed C(sp3)–H functionalization is provided. In addition, mechanistic hypothesis and general aspects of these reactions have also been summarized. Finally, the limitations and perspectives on nickel-catalyzed C–H functionalization are discussed.
【Fund】: 国家重点基础研究发展计划(2015CB856600);; 国家自然科学基金(21402170)资助
【CateGory Index】: O643.32
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【Citations】
Chinese Journal Full-text Database 3 Hits
1 Ma,Yuyong Li,Wei Yu,Biao*(State Key Laboratory of Bioorganic and Natural Products Chemistry,Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences,Shanghai 200032);Regio-selective Dehydrogenation on the D or E Rings of Oleanolic Acid by Pd-Promoted C—H Activation[J];Acta Chimica Sinica;2013-04
2 XU ZeJun;JIAO Ning;State Key Laboratory of Natural and Biomimetic Drugs;School of Pharmaceutical Sciences, Peking University;;Activation and controlled transformation of inactive chemical bonds[J];Scientia Sinica(Chimica);2013-09
3 Sheng Zhao;Fa-Jie Chen;Bin Liu;Bing-Feng Shi;Department of Chemistry, Zhejiang University;;Copper-catalyzed direct acyloxylation of C(sp~2)–H bonds with Benzoic acids[J];中国科学:化学(英文版);2015-08
【Co-citations】
Chinese Journal Full-text Database 7 Hits
1 Zisong Qi;Xingwei Li;Dalian Institute of Chemical Physics, Chinese Academy of Sciences;;Rh(Ⅲ)-catalyzed C–H activation of benzamides:Coupling with quinones[J];Chinese Journal of Catalysis;2015-01
2 Chen Hualei;Li Sifeng;Xu Jianbin;Yang Qingjing;Liu Shanshan;Zhou Yongyun;Huang Chao;Fan Baomin;Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan University of Nationalities;;Palladium-Catalyzed Ring-Opening Reaction of Oxa/Azabenzonorbornadienes with Aryl Acetylenes[J];Acta Chimica Sinica;2013-09
3 Cheng,Yunfei;Chen,Lifang;Qi,Zhiwen;He,Heyong;The Third Research Institute of Ministry of Public Security;State Key Laboratory of Chemical Engineering,East China University of Science and Technology;Department of Chemistry,Fudan University;;Pd_3Bi_2W_(22)/SBA-15 as a Heterogeneous Catalyst for n-Hexadecane Oxidation[J];Acta Chimica Sinica;2013-10
4 Liu,Dingjia;Yu,Haizhu;Fu,Yao;Department of Chemistry,University of Science and Technology of China;Department of Polymer Science and Engineering,University of Science and Technology Beijing;;DFT Study on Mechanism of Ruthenium-catalyzed meta Sulfonation[J];Acta Chimica Sinica;2013-10
5 Zhang,Qian;Lü,Yunhe;Li,Yan;Xiong,Tao;Zhang,Qian;Department of Chemistry,Northeast Normal University;;Copper-Catalyzed Benzylic sp~3 C-H Amination Reaction of Amidines:Synthesis of Quinazoline Derivatives[J];Acta Chimica Sinica;2014-11
6 DING Cheng-rong;YANG Jian;ZHANG Guo-fu;College of Chemical Engineering,Zhejiang University of Technology;;Synthesis of 3-Iodo-N~1-(2-methyl-4-perfluoropropane-2-yl)-N~2-[2-methyl-1-(methylsulfinyl) propan-2-yl phenyl]phthalamide[J];Fine Chemicals;2015-01
7 Bo Wang;Gang He;Gong Chen;Department of Chemistry, the Pennsylvania State University, University Park;;Synthesis of β-alkynyl α-amino acids via palladium-catalyzed alkynylation of unactivated C(sp~3)-H bonds[J];中国科学:化学(英文版);2015-08
China Proceedings of conference Full-text Database 2 Hits
1 Bing-Feng Shi;Qi Zhang;Kai Chen;Fa-Jie Chen;Xue-Song Yin;Department of Chemistry, Zhejiang University;;Pd-Catalyzed Functionalization of Unactivated C(sp~3)–H Bonds[A];[C];2014
2 Bing-Feng Shi;;Pd-Catalyzed Direct Functionalization of Unactivated C(sp~3)-H Bonds[A];[C];2014
【Secondary Citations】
Chinese Journal Full-text Database 1 Hits
1 Ma,Yuyong Li,Wei Yu,Biao*(State Key Laboratory of Bioorganic and Natural Products Chemistry,Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences,Shanghai 200032);Regio-selective Dehydrogenation on the D or E Rings of Oleanolic Acid by Pd-Promoted C—H Activation[J];Acta Chimica Sinica;2013-04
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