[1]李 轩,张 敬.可见光诱导过渡金属催化的C-H功能化研究进展[J].南京师大学报(自然科学版),2021,44(03):45-53.[doi:10.3969/j.issn.1001-4616.2021.03.008]
　Li Xuan,Zhang Jing.Visible Light-Induced Transition Metal-Catalyzed C-H Functionalization[J].Journal of Nanjing Normal University(Natural Science Edition),2021,44(03):45-53.[doi:10.3969/j.issn.1001-4616.2021.03.008]
点击复制

可见光诱导过渡金属催化的C-H功能化研究进展()
分享到：

《南京师大学报（自然科学版）》[ISSN:1001-4616/CN:32-1239/N]

卷:
第44卷
期数:
2021年03期
页码:
45-53
栏目:
·化学·
出版日期:
2021-09-15

文章信息/Info

Title:
Visible Light-Induced Transition Metal-Catalyzed C-H Functionalization
文章编号:
1001-4616(2021)03-0045-09
作者:
李 轩; 张 敬
武汉大学高等研究院,湖北 武汉 430072
Author(s):
Li Xuan; Zhang Jing
The Institute for Advanced Studies,Wuhan University,Wuhan 430072,China
关键词:
光催化; 过渡金属催化; 可见光; 激发态; C-H功能化
Keywords:
photocatalysis; transition metal catalysis; visible light; excited state; C-H functionalization
分类号:
O621.3
DOI:
10.3969/j.issn.1001-4616.2021.03.008
文献标志码:
A
摘要:
可见光诱导过渡金属催化已成为一种新型的光催化反应,在过去的几年中得到快速的发展. 与传统的光催化剂催化或光催化剂与过渡金属协同催化不同,可见光诱导过渡金属催化中过渡金属络合物为唯一催化剂,它既能够吸收可见光将光能转化为化学能又参与化学键的断裂与形成,在催化循环中起到“双重作用”. 相比于传统的基于基态过渡金属络合物参与的热反应,可见光诱导过渡金属催化是利用激发态过渡金属络合物的反应特性,使得反应条件更温和,底物范围更广,选择性更好. 本文概述了可见光诱导过渡金属催化的C-H功能化最新进展. 本综述内容按C(sp3)-H和C(sp2)-H功能化分类,涉及Pd、Co、Mn、Ir、Rh和Ru金属催化剂参与的C-H键的远程去饱和化、烷基化、芳基化、硼基化、氨基化等反应类型.
Abstract:
Visible light-induced transition metal catalysis has become a new type of photocatalytic reaction,which has been rapidly developed in the past few years. Different from the conventional photocatalyst and photocatalyst/transition metal(TM)synergistic catalysis,transition metal complex is the only catalyst in visible light-induced transition metal catalysis. It can not only absorb visible light to convert light energy into chemical energy,but also participate in the cleavage and formation of chemical bonds,playing a dual role in the catalytic cycle. Compared with the traditional transition metal catalysis based on the thermal reaction of the ground state transition metal complex,visible light-induced transition metal catalysis utilizes the unique reactivity of excited transition metal complexes,giving milder reaction conditions,wider substrate scopes,and better selectivity. This review summarizes the latest developments in visible light-induced transition metal catalytic C-H functionalization. The content of this review is classified according to C(sp3)-H and C(sp2)-H functionalization,involving the C-H remote desaturation,alkylation,arylation,amination,borylation and other types of reactions involving Pd,Co,Mn,Ir,Rh,and Ru metal catalysts.

参考文献/References:

[1] MAGANO J,DUNETZ J R. Large-scale applications of transition metal-catalyzed couplings for the synthesis of pharmaceuticals[J]. Chemical revivews,2011,111(3):2177-2250. [2]YANG M,LI J,CHEN P R. Transition metal-mediated bioorthogonal protein chemistry in living cells[J]. Chemical society reviews,2014,43(18):6511-6526. [3]俞星辰,肖亚平,韩维. 铁催化过氧化氢氧化端炔合成羧酸类化合物[J]. 南京师大学报(自然科学版),2020,43(2):29-33. [4]ARIAS-ROTONDO D M,MCCUSKER J K. The photophysics of photoredox catalysis:a road map for catalyst design[J]. Chemical society reviews,2016,45(21):5803-5820. [5]ROMERO N A,NICEWICZ D A. Organic photoredox catalysis[J]. Chemical reviews,2016,116(17):10075-10166. [6]SHAW M H,TWILTON J,MACMILLAN D W. Photoredox catalysis in organic chemistry[J]. Journal of organic chemistry,2016,81(16):6898-6926. [7]SKUBI K L,BLUM T R,YOON T P. Dual catalysis strategies in photochemical synthesis[J]. Chemical reviews,2016,116(17):10035-10074. [8]WANG C S,DIXNEUF P H,SOULE J F. Photoredox catalysis for building C-C bonds from C(sp2)-H bonds[J]. Chemical reviews,2018,118(16):7532-7585. [9]PARASRAM M,GEVORGYAN V. Visible light-induced transition metal-catalyzed transformations:beyond conventional photosensitizers[J]. Chemical society reviews,2017,46(20):6227-6240. [10]CHENG W M,SHANG R. Transition metal-catalyzed organic reactions under visible light:recent developments and future perspectives[J]. ACS catalysis,2020,10(16):9170-9196. [11]HUANG X,MEGGERS E. Asymmetric photocatalysis with bis-cyclometalated rhodium complexes[J]. Accounts of chemical research,2019,52(3):833-847. [12]PARASRAM M,CHUENTRAGOOL P,SARKAR D,et al. Photoinduced formation of hybrid aryl Pd-radical species capable of 1,5-HAT:selective catalytic oxidation of silyl ethers into silyl enol ethers[J]. Journal of the American Chemical Society,2016,138(20):6340-6343. [13]PARASRAM M,CHUENTRAGOOL P,WANG Y,et al. General,auxiliary-enabled photoinduced Pd-catalyzed remote desaturation of aliphatic alcohols[J]. Journal of the American Chemical Society,2017,139(42):14857-14860. [14]CHUEN-TRAGOOL P,PARASRAM M,SHI Y,et al. General,mild,and selective method for desaturation of aliphatic amines[J]. Journal of the American Chemical Society,2018,140(7):2465-2468. [15]RATUSHNYY M,PARASRAM M,WANG Y,et al. Palladium-catalyzed atom-transfer radical cyclization at remote unactivated C(sp3)-H sites:hydrogen-atom transfer of hybrid vinyl palladium radical intermediates[J]. Angewandte chemie international edition,2018,57(10):2712-2715. [16]CHUEN-TRAGOOL P,YADAGIRI D,MORITA T,et al. Aliphatic radical relay heck reaction at unactivated C(sp3)-H sites of alcohols[J]. Angewandte chemie international edition,2019,58(6):1794-1798. [17]RATUSHNYY M,KVASOVS N,SARKAR S,et al. Visible-light-induced palladium-catalyzed generation of aryl radicals from aryl triflates[J]. Angewandte chemie international edition,2020,59(26):10316-10320. [18]TO W P,LIU Y,LAU T C,et al. A robust palladium(II)-porphyrin complex as catalyst for visible light induced oxidative C-H functionalization[J]. Chemistry—a European journal,2013,19(18):5654-5664. [19]ZHOU W J,CAO G M,SHEN G,et al. Visible-light-driven palladium-catalyzed radical alkylation of C-H bonds with unactivated alkyl bromides[J]. Angewandte chemie international edition,2017,56(49):15683-15687. [20]HUO H,SHEN X,WANG C,et al. Asymmetric photoredox transition-metal catalysis activated by visible light[J]. Nature,2014,515(7525):100-103. [21]HUO H,WANG C,HARMS K,et al. Enantioselective,catalytic trichloromethylation through visible-light-activated photoredox catalysis with a chiral iridium complex[J]. Journal of the American Chemical Society,2015,137(30):9551-9554. [22]FERNANDEZ-ALVAREZ V M,MASERAS F. Computational characterization of the mechanism for the light-driven catalytic trichloromethylation of acylpyridines[J]. Organic & biomolecular chemistry,2017,15(40):8641-8647. [23]MEGGERS E,HUO H,HUANG X,et al. Visible-light-activated enantioselective perfluoroalkylation with a chiral iridium photoredox catalyst[J]. Synlett,2015,27(5):749-753. [24]WANG C,ZHENG Y,HUO H,et al. Merger of visible light induced oxidation and enantioselective alkylation with a chiral iridium catalyst[J]. Chemistry—a European journal,2015,21(20):7355-7359. [25]TAN Y,YUAN W,GONG L,et al. Aerobic asymmetric dehydrogenative cross-coupling between two C(sp3)-H groups catalyzed by a chiral-at-metal rhodium complex[J]. Angewandte chemie international edition,2015,54(44):13045-13048. [26]SHEN X,HARMS K,MARSCH M,et al. A rhodium catalyst superior to iridium congeners for enantioselective radical amination activated by visible light[J]. Chemistry—a European journal,2016,22(27):9102-9105. [27]STEINLANDT P S,ZUO W,HARMS K,et al. Bis-cyclometalated indazole chiral-at-rhodium catalyst for asymmetric photoredox cyanoalkylations[J]. Chemistry—a European journal,2019,25(67):15333-15340. [28]MA J,ROSALES A R,HUANG X,et al. Visible-light-activated asymmetric beta-C-H functionalization of acceptor-substituted ketones with 1,2-Dicarbonyl compounds[J]. Journal of the American Chemical Society,2017,139(48):17245-17248. [29]FU Y,SHANG R,WANG G Z. Irradiation-induced palladium-catalyzed direct C-H alkylation of heteroarenes with tertiary and secondary alkyl bromides[J]. Synthesis,2018,50(15):2908-2914. [30]JIAO Z,LIM L H,HIRAO H,et al. Palladium-catalyzed para-selective alkylation of electron-deficient arenes[J]. Angewandte chemie international edition,2018,57(21):6294-6298. [31]NUHANT P,ODERINDE M S,GENOVINO J,et al. Visible-light-initiated manganese catalysis for C-H alkylation of heteroarenes:applications and mechanistic studies[J]. Angewandte chemie international edition,2017,56(48):15309-15313. [32]LIANG Y F,STEINBOCK R,YANG L,et al. Continuous visible-light photoflow approach for a manganese-catalyzed(Het)arene C-H arylation[J]. Angewandte chemie international edition,2018,57(33):10625-10629. [33]PAL A K,LI C,HANAN G S,et al. Blue-emissive cobalt(III)complexes and their use in the photocatalytic trifluoromethylation of polycyclic aromatic hydrocarbons[J]. Angewandte chemie international edition,2018,57(27):8027-8031. [34]HSU Y C,WANG V C,AU-YEUNG K C,et al. One-pot tandem photoredox and cross-coupling catalysis with a single palladium carbodicarbene complex[J]. Angewandte chemie international edition,2018,57(17):4622-4626. [35]THONGPAEN J,MANGUIN R,DORCET V,et al. Visible light induced rhodium(I)-catalyzed C-H borylation[J]. Angewandte chemie international edition,2019,58(43):15244-15248. [36]GANDEEPAN P,KOELLER J,KORVORAPUN K,et al. Visible-light-enabled ruthenium-catalyzed meta-C-H alkylation at room temperature[J]. Angewandte chemie international edition,2019,58(29):9820-9825. [37]SAGADEVAN A,GREANEY M F. meta-selective C-H activation of arenes at room temperature using visible light:dual-function ruthenium catalysis[J]. Angewandte chemie international edition,2019,58(29):9826-9830. [38]SAGADEVAN A,CHARITOU A,WANG F,et al. Ortho C-H arylation of arenes at room temperature using visible light ruthenium C-H activation[J]. Chemical science,2020,11(17):4439-4443. [39]KORVORAPUN K,STRUWE J,KUNIYIL R,et al. Photo-induced ruthenium-catalyzed C-H arylations at ambient temperature[J]. Angewandte chemie international edition,2020,59(41):18103-18109.

相似文献/References:

[1]余伊丽,唐 剑,应椰琦,等.光催化的含吸电子基团卤代苯的偶联反应[J].南京师大学报(自然科学版),2014,37(02):75.
　Yu Yili,Tang Jian,Ying Yeqi,et al.Photocatalytic Coupling Reactions of Halobenzenes With an Electron Withdrawing Group[J].Journal of Nanjing Normal University(Natural Science Edition),2014,37(03):75.
[2]韩维,钟延珍,金凤莉,等.Suzuki羰基化反应的最新研究进展[J].南京师大学报(自然科学版),2015,38(03):1.
　HanWei,ZhongYanzhen,JinFengli,et al.RecentProgressinCarbonylativeSuzukiReaction[J].Journal of Nanjing Normal University(Natural Science Edition),2015,38(03):1.
[3]叶　景,李海利,李秋明,等.I-TiO2负载活性炭的制备及其光催化再生[J].南京师大学报(自然科学版),2016,39(02):22.[doi:10.3969/j.issn.1001-4616.2016.02.005]
　Ye Jing,Li Haili,Li Qiuming,et al.Preparation of Activated Carbon Loaded I-TiO2and Its Photocatalytic Regeneration[J].Journal of Nanjing Normal University(Natural Science Edition),2016,39(03):22.[doi:10.3969/j.issn.1001-4616.2016.02.005]
[4]陈宗华,陈 杰,汪 琼,等.气提-光催化组合工艺再生饱和吸附甲苯的活性炭[J].南京师大学报(自然科学版),2017,40(04):80.[doi:10.3969/j.issn.1001-4616.2017.04.013]
　Chen Zonghua,Chen Jie,Wang Qiong,et al.Gas Stripping-Photocatalysis Combined Process RegeneratedActivated Carbon Saturated by Toluene[J].Journal of Nanjing Normal University(Natural Science Edition),2017,40(03):80.[doi:10.3969/j.issn.1001-4616.2017.04.013]
[5]张 政,郏建奎,蒋彩云,等.NaOH浓度对水热合成TiO2纳米管形成及光催化性能的影响[J].南京师大学报(自然科学版),2018,41(03):52.[doi:10.3969/j.issn.1001-4616.2018.03.009]
　Zhang Zheng,Jia Jiankui,Jiang Caiyun,et al.Effect of NaOH Concentration on Formation and Photocatalytic Performanceof TiO2 Nanotubes Prepared by Hydrothermal Method[J].Journal of Nanjing Normal University(Natural Science Edition),2018,41(03):52.[doi:10.3969/j.issn.1001-4616.2018.03.009]
[6]刘国清,金 懿,吕延文,等.Ce4+掺杂ZnO纳米材料的制备及其光催化性能研究[J].南京师大学报(自然科学版),2019,42(02):93.[doi:10.3969/j.issn.1001-4616.2019.02.015]
　Liu Guoqing,Jin Yi,Lü Yanwen,et al.Preparation and Photocatalytic Properties ofCe4+-doped ZnO Nano Materials[J].Journal of Nanjing Normal University(Natural Science Edition),2019,42(03):93.[doi:10.3969/j.issn.1001-4616.2019.02.015]
[7]黄文鑫,郏建奎,李攀杰,等.BiOCl/TiO2对四环素-铜复合物的光催化降解研究[J].南京师大学报(自然科学版),2020,43(04):14.[doi:10.3969/j.issn.1001-4616.2020.04.004]
　Huang Wenxin,Jia Jiankui,Li Panjie,et al.Photocatalytic Degradation of Tetracycline-Copper Complex by BiOCl/TiO2[J].Journal of Nanjing Normal University(Natural Science Edition),2020,43(03):14.[doi:10.3969/j.issn.1001-4616.2020.04.004]

备注/Memo

备注/Memo:
收稿日期:2021-04-08. 基金项目:中央高校基本科研业务费专项(2042019kf0008). 通讯作者:张敬,博士,教授,博士生导师,研究方向:有机合成化学. E-mail:jzhangwhu@whu.edu.cn
更新日期/Last Update: 2021-09-15