EDITORIAL BOARD AND ADVISORY BOARD OF ACTA CHIMICA SINICA

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2 Editor-in-Chief ZHU Qi-Lin( ) Nankai University Associate Editors EDITRIAL BARD AND ADVISRY BARD F ACTA CHIMICA SINICA DING Kui-Ling( ) Shanghai Institute of rganic Chemisry, CAS HE Chuan( ) University of Chicago, USA LIU Zhong-Fan( ) Peking University ZHANG Xi( ) Tsinghua University WANG Li-Xiang( ) Changchun Institute of Applied Chemistry, CAS Editorial Board (Alphabetically arranged) GA Song( ) Peking University JIANG Gui-Bin( ) Research Center for Eco-Environmental Sciences, CAS SUN Shi-Gang( ) Xiamen University SHUAI Zhi-Gang( ) Tsinghua University CHEN Chuan-Feng( ) CHEN Jun( ) CHEN Peng( ) CHEN Yong-Sheng( ) CUI Chun-Ming( ) DENG Zhao-Xiang( ) DING Kui-Ling( ) FAN Chun-Hai( ) FAN Qing-Hua( ) FENG Xiao-Ming( ) FU Yao( ) GA Song( ) GNG Liu-Zhu( ) HE Chuan( ) HU Yang-Long( ) HU Jin-Bo( ) HU Min( ) HU Wen-Hao( ) HU Zheng( ) HUANG Fei( ) HUANG Fei-He( ) HUANG Pei-Qiang( ) JIANG Gui-Bin( ) LI Zhan-Ting( ) LI Jing-Hong( ) LIU Dong-Sheng( ) LIU Guo-Sheng( ) LIU Hai-Chao( ) LIU Jing-Fu( ) LIU Lei( ) LIU Yu( ) LIU Zhong-Fan( ) LNG Yi-Tao( ) MA Jun-An( ) MENG Qing-Bo( ) PAN Yuan-Jiang( ) PENG Hui-Sheng( ) PENG Xiao-Jun( ) QU Liang-Ti( ) REN Bin( ) SHUAI Zhi-Gang( ) SNG Yan-Lin( ) SUN Shi-Gang( ) TNG Ming-Liang( ) WANG Guan-Wu( ) WANG Li-Xiang( ) WANG Peng( ) WANG Shu( ) WANG Wei( ) WANG Xun( ) XI Zhen-Feng( ) XIA Yong-Yao( ) XU Jing-Juan( ) YANG Huang-Hao( ) YU Shu-Li( ) YU Gui( ) YU Jia-Guo( ) YU Zhi-Xiang( ) YU Biao( ) ZHANG Jin( ) ZHANG Li-Zhi( ) ZHANG Xi( ) ZHANG Ya-Wen( ) ZHENG Li-Min( ) ZHU Jian( ) ZHU Qi-Lin( ) ZHU Guang-Shan( ) ZHUANG Lin( ) Advisory Board AN Li-Jia( ) CHE Chi-Ming( ) CHEN Er-Qiang( ) CHEN Yi( ) CHENG Yi-Yu( ) DAI Li-Xin( ) FAN Kang-Nian( ) FENG Shou-Hua( ) GA Zi( ) GU Qing-Xiang( ) HA Jing-Cheng( ) Henry N. C. WNG( ) HNG Mao-Chun( ) HU Xue-Long( ) HU Ying( ) HU Yue-Fei( ) JI Guo-Zhen( ) LI Hao-Ran( ) LI Jun-Bai( ) LI Le-Min( ) LIA Dai-Zheng( ) LIN Guo-Qiang( ) LÜ Long( ) LU Xi-Yan( ) MA Chun-An( ) MA Sheng-Ming( ) SHEN Yan-Chang( ) SNG Li-Cheng( ) SU Qiang( ) TIAN Wei-Sheng( ) WAN Hui-Lin( ) WANG De-Zheng( ) WANG Er-Kang( ) WANG Mei-Xiang( ) WU Yi-Kang( ) WU Yu-Lin( ) YANG Yu-Liang( ) YA Jian-Nian( ) YE Jian-Nong( ) ZHA Dong-Yuan( ) ZHA Yu-Fen( ) ZHANG Yu-Kui( ) ZHENG Lan-Sun( ) ZHU Yong-Fa( ) ZU Han-Fa( )

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5 Editorial,.,., G. Ciamician P. Silber.,.,..,,.,,,.,,.,,, : 1, ;,, ; 2., ;,,, ; 3,..,,,,,.,, 3,4- DI: /A ;, - -,, - DI: /A ; - 1,6-, - -, '- DI: / Acta Chim. Sinica 2017, 75, Shanghai Institute of rganic Chemistry, Chinese Academy of Sciences 5

6 A ;, 2, DI: /A ;, DI: /A Ru(bpy) 3 Cl 2, Togni s, DI: /A ;, DI: /A ;, 1,4, DI: /A ;, 2- DI: /A C H DI: /A ; DI: /A ;, DI: /A ;, DI: /A ; DI: /A ,.,, Fe I -C-Fe I, [FeFe] DI: / A ; DI: /A ; DI: /A ,.,,,,,, Ding, Kuiling a Xiao, Wenjing b Wu, Li-Zhu c ( a State Key Laboratory of rganometallic Chemistry, Shanghai Institute of rganic Chemistry, Chinese Academy of Sciences, Shanghai ) ( b Key Laboratory of Pesticide & Chemical Biology Ministry of Education and College of Chemistry, Central China Normal University, Wuhan ) ( c Key Laboratory of Photochemical Conversion and ptoelectronic Materials, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing ) Shanghai Institute of rganic Chemistry, Chinese Academy of Sciences Acta Chim. Sinica 2017, 75, 5 6

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8 ......,, *,,, 2017, 75(1), : Fe 2 (N 2 C 5 H 10 )(C) 6-x (PR 3 ) x......,,,, *,,, 2017, 75(1), , *,,, *,, 2017, 75(1), ,,,,, *,, 2017, 75(1), C-H......,,, *,, 2017, 75(1), ,, *, *,, 2017, 75(1), ,, *,, 2017, 75(1), Shanghai Institute of rganic Chemistry, Chinese Academy of Sciences Acta Chim. Sinica 2017, 75, 7 8

9 ACTA CHIMICA SINICA Vol. 75, No. 1 January 15, 2017 Contents n the cover: A strategy of photocatalytic oxidative deprotonation electron transfer was developed for the direct generation of amidyl radicals and their application to radical hydroamination reaction. [Chen, Jiarong et al. on page ] Editorial rganic Photochemistry The Road to Glory Ding, Kuiling; Xiao, Wenjing; Wu, Li-Zhu Acta Chim. Sinica 2017, 75(1), 5-6 Highlight Visible Light Promoted Benzylic C sp3 H Activation and Functionalization Benzylic C sp3 -H Activation and Functionalization: H X X = C, N, FG X single electron transfer sustainable, green, efficient Reaction Intermediate: Pei, Pengkun; Zhang, Fan; Yi, Hong; Lei, Aiwen* Acta Chim. Sinica 2017, 75(1), Perspective Photo-induced Catalytic Asymmetric Free Radical Reactions + N + + Wang, Dehong; Zhang, Long; Luo, Sanzhong* Acta Chim. Sinica 2017, 75(1), This perspective shows how light joins force with chiral catalysts to manipulate free radical intermediates in a stereospace. Acta Chim. Sinica 2017, 75, Shanghai Institute of rganic Chemistry, Chinese Academy of Sciences 9

10 Content Review Visible Light Induced Cross-Coupling Hydrogen Evolution Reactions Zhong, Jian-Ji; Meng, Qing-Yuan; Chen, Bin; Tung, Chen-Ho; Wu, Li-Zhu* Acta Chim. Sinica 2017, 75(1), A new chemical reaction, namely cross-coupling hydrogen evolution (CCHE) reaction, is highlighted. In contrast to traditional strategies, the CCHE reaction is efficient and powerful for construction of a series of chemical bonds accompanying with an equivalent of H 2 as the sole byproduct, with no use of any external oxidant at ambient condition. Visible-Light-Induced Carboxyl and Alkoxyl Radical Generations and Reactions Zhang, Jing; Chen, Yiyun* Acta Chim. Sinica 2017, 75(1), The carboxyl and alkoxyl radicals generated from visible light photoredox reactions are important reaction intermediates in organic synthesis, which have witnessed conceivable progress recently. In this review, we focus on visible-light-induced photoredox methods to generate carboxyl radicals from carboxylate derivatives and carboxylates, as well as alkoxyl radicals from alcohol derivatives and alcohols, and briefly discuss their synthetic applications. Advances in Ru(II)-based Photoactivated Chemotherapy Agents Zhou, Qianxiong*; Wang, Xuesong* Acta Chim. Sinica 2017, 75(1), Ru(II) complexes with photolabile ligands can bind DNA covalently upon irradiation, thus may find promising application in photoactivated chemotherapy (PACT) to achieve high selectivity and low side effects by virtue of the spatiotemporal control of irradiation. In this review, the recent progress in Ru(II)-based PACT agents was fully discussed and a perspective for their future development was included. Communication Visible Light Promoted Carbodifluoroalkylation of Homopropargylic Alcohols via Concomitant 1,4-Aryl Migration Zhou, Nengneng; Xu, Pan; Li, Weipeng; Cheng, Yixiang; Zhu, Chengjian* Acta Chim. Sinica 2017, 75(1), R 1 H Ar R R 1 =H,Me,Ar + BrCF 2 C 2 Et visible light fac-ir(ppy) 3 1,4-Aryl Migration Ar R CF 2 C 2 Et A novel visible light promoted carbodifluoroalkylation of homopropargylic alcohols was described. A series of difluoro 5-oxopentanoate compounds were obtained through a tandem radical addition and 1,4-aryl migration. R Shanghai Institute of rganic Chemistry, Chinese Academy of Sciences Acta Chim. Sinica 2017, 75, 9 13

11 Content Visible-Light Induced Trifluoromethylation of Internal lefinic C H Bonds through Photoredox Catalysis Gou, Baoquan; Yang, Chao*; Zhang, Lei; Xia, Wujiong* Acta Chim. Sinica 2017, 75(1), An approach for direct trifluoromethylation of internal olefins of -oxoketene dithioacetals has been achieved by using Ru(bpy) 3 Cl 2 as photocatalyst and Togni s reagent as trifluoromethylating agent under irradiation with visible light. This protocol provides an efficient and easy access to prepare trifluoromethylated dithioalkyl -oxoketene acetals under mild conditions, and is highlighted by its operational simplicity and avoiding using toxic reagent. Furthermore, the gram-scale reaction suggested the potential application of this protocol in organic synthesis. Visible Light Mediated Photocatalytic Aerobic Dehydrogenation: A General and Direct Approach to Access 2,3-Dihydro-4-Pyridones and 4-Quinolones Shao, Tianju; Jiang, Zhiyong* Acta Chim. Sinica 2017, 75(1), By using dicyanopyrazine-derived chromophore (DPZ) as the photocatalyst, a visible-light-induced photocatalytic aerobic dehydrogenation of 4-piperidones and 2,3-dihydro-4-quinolones has been developed, affording two series of valuable N-containing heterocycles, i.e. 2,3-dihydro-4-pyridones and 4-quinolones, with satisfactory results (up to 75% yield). Decarboxylative 1,6-Conjugate Addition of -Keto Acids with para- Quinone Methides Enabled by Photoredox Catalysis Wu, Zijun; Wang, Jian* Acta Chim. Sinica 2017, 75(1), Decarboxylative 1,6-conjugate addition of -keto acids with para-quinone methides mediated by photoredox catalysis provided various -keto-, '-diaryl ketones in moderate to excellent yields. Benzothiadiazole Conjugated Metalorganic Framework for rganic Aerobic xidation Reactions under Visible Light Zhang, Wen-Qiang; Li, Qiu-Yan*; Yang, Xinyu; Ma, Zheng; Wang, Huanhuan; Wang, Xiao-Jun* Acta Chim. Sinica 2017, 75(1), A benzothiadiazole conjugated Zr(IV) metal-organic framework exhibits a highly efficient photocatalytic activity toward organic aerobic oxidation reactions driven by visible light. Acta Chim. Sinica 2017, 75, Shanghai Institute of rganic Chemistry, Chinese Academy of Sciences 11

12 Content Article Visible Light Photocatalytic N-Radicalbased Intramolecular Hydroamination of Benzamides Yu, Xiaoye; Zhou, Fan; Chen, Jiarong*; Xiao, Wenjing Acta Chim. Sinica 2017, 75(1), Azo-bridged New Diiron Carbonyl Complex: Synthesis of Fe 2 (NR) 2 - (C) 6-x (PR 3 ) x and the Derivatives A transition-metal free and visible light photocatalytic N-radical-based intramolecular hydroamination of benzamides has been reported. The reaction provides a practical and efficient approach to various biologically important 3,4-dihydroisoquinolinones with generally high yields. The sunlight irradiation reaction and gram-scale reaction also highlighted the potential synthetic utility of this method. NH "rotated"structure Me [S 4 Fe 4 ] S S N N Ph C 2 Cys S Fe Fe P Fe Fe Fe Fe C CN C C C P CN C C C Ph C 2 Me Li, Ran; Xu, Wenyuan; Zhao, Jinqin; Yu, Xin; Wang, Wenguang*; Tung, Chen-Ho Acta Chim. Sinica 2017, 75(1), As a new synthetic model for the H red state of [FeFe]-H 2 ase, Fe(I)Fe(I) compound Fe 2 (N 2 C 5 H 10 )( -C)(C) 4 (dppbz) featuring Fe-C-Fe fragment was synthesized, and its rotated structure was revealed by X-ray crystallographic analysis. Pyrenyl Peripheral-Decorated Polyamidoamine Dendrimer for Fluorescent Temperature Detection in Aqueous Phase Qin, Tianyi; Zeng, Yi*; Chen, Jinping; Yu, Tianjun; Li, Yi* Acta Chim. Sinica 2017, 75(1), Pyrenyl-decorated G2 PAMAM was prepared and the temperature-sensitive fluorescence was investigated, showing the capability of temperature detection in aqueous phase. Radical Fluoroalkylation of Aryl Alkenes with Fluorinated Sulfones by Visible-Light Photoredox Catalysis Rong, Jian; Ni, Chuanfa; Wang, Yunze; Kuang, Cuiwen; Gu, Yucheng; Hu, Jinbo* Acta Chim. Sinica 2017, 75(1), The radical fluoroalkylation of aryl alkenes with fluorinated sulfones has been achieved under visible light photoredox catalysis. Various fluoroalkyl radicals, including trifluoromethyl (CF 3 ), difluoromethyl (HCF 2 ), 1,1-difluoroethyl (CH 3 CF 2 ) and (phenyl)- difluoromethyl (PhCF 2 ) radicals, can be incorporated into styrene derivatives via this method Shanghai Institute of rganic Chemistry, Chinese Academy of Sciences Acta Chim. Sinica 2017, 75, 9 13

13 Visible-Light Photoredox Catalytic -Cyanation Reactions of Tertiary Amines R 3 R 1 N R 2 CN I H or + R H visible light safe cyanide source photoredox catalysis redox-neutral room-temperature R 3 R 1 N R 2 CN R or Content CN 18 examples up to 93% yield Zhou, Quanquan; Liu, Dan; Xiao, Wenjing; Lu, Liangqiu* Acta Chim. Sinica 2017, 75(1), A visible-light photoredox catalytic -cyanation reaction of tertiary amines has been developed by using cyanobenziodoxol as a stable and safe cyanide source. This protocol is favored for mild conditions, the avoidance of extra oxidant and highly toxic cyano anion, good functional tolerance as well as safe and simple operations. By doing so, a variety of -aminonitriles are afforded in good to excellent yields. A sunlight-driven reaction and a gram-scale reaction further demonstrate the utility of this methodology. In addition, the same strategy was further successfully applied to the decarboxylative cyanation of carboxylic acids. Halogen-Bond-Promoted Radical Isocyanide Insertion of o-diisocyanoarenes with Perfluoroalkyl Bromides under Visible Light Irradiation Sun, Xiaoyang; Wang, Wenmin; Ma, Jing*; Yu, Shouyun* Acta Chim. Sinica 2017, 75(1), A halogen-bond-promoted double radical isocyanide insertion of o-diisocyanoarenes with perfluoroalkyl bromides is reported. Visible-Light-Driven Aromatization Hydrogen Evolution by rganic Dye and Ni Complex Dihydroheteroaromatics Br visible light + Br H H N N Ni Na + Br Br Na + H H Wang, Xiaoju; Dong, Kui; Liu, Qiang* Acta Chim. Sinica 2017, 75(1), Heteroaromatics + H 2 Combining eosin Y and nickel complex as the photocatalyst and the hydrogen evolution catalyst, several types of dihydroheteroaromatics produced corresponding heteroaromatics and molecular hydrogen under visible-light irradiation at room temperature. Acta Chim. Sinica 2017, 75, Shanghai Institute of rganic Chemistry, Chinese Academy of Sciences 13

14 SCI ( ) Huaxue Xuebao ACTA CHIMICA SINICA (Monthly) 1933 (Founded in 1933) 75 1 Vol. 75 No January 15, 2017 Supervised by Chinese Academy of Sciences Sponsored by The Chinese Chemical Society and Shanghai Institute of rganic Chemistry, Chinese Academy of Sciences Editor-in-Chief: ZHU Qi-Lin ( 345, ) Edited and Published by Editorial ffice of Acta Chimica Sinica (345 Lingling Lu, Shanghai , China) Printed by Shanghai Newcabo Business Printing Co., Ltd. Subscriptions Domestic: Local Post ffices ( 399 ) Foreign: China International Book Trading Corporation (P.. Box 399, Beijing, China) hxxb@sioc.ac.cn ISSN CN / M : Tel: ; slyou@sioc.ac.cn Shanghai Institute of rganic Chemistry, Chinese Academy of Sciences Acta Chim. Sinica 2017, 75, 14 14