Unreactive C-N Bond Activation of Anilines via Photoinduced Aerobic Borylation

被引:14
作者
Ji, Shuohan [1 ,2 ,3 ]
Qin, Shengxiang [1 ,2 ,3 ]
Yin, Chunyu [1 ,2 ]
Luo, Lu [1 ,2 ]
Zhang, Hua [1 ,2 ,3 ]
机构
[1] South Cent Univ Nationalities, Key Lab Catalysis & Energy Mat Chem, Minist Educ, Wuhan 430074, Peoples R China
[2] South Cent Univ Nationalities, Hubei Key Lab Catalysis & Mat Sci, Wuhan 430074, Peoples R China
[3] Nanchang Univ, Coll Chem, Nanchang 330031, Jiangxi, Peoples R China
基金
中国国家自然科学基金;
关键词
CARBON-NITROGEN BONDS; CATALYZED CLEAVAGE; ARYL; SALTS; ORGANOBORANES; DERIVATIVES; CONVERSION; AMINES; OXYGEN;
D O I
10.1021/acs.orglett.1c03590
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Unreactive C-N bond activation of anilines was achieved by photoinduced aerobic borylation. A diverse range of tertiary and secondary anilines were converted to aryl boronate esters in moderate to good yields with wide functional group tolerance under simple and ambient photochemical conditions. This transformation achieved the direct and facile C-N bond activation of unreactive anilines, providing a convenient and practical route transforming widely available anilines into useful aryl boronate esters.
引用
收藏
页码:64 / 68
页数:5
相关论文
共 45 条
[1]   The first Suzuki cross-couplings of aryltrimethylammonium salts [J].
Blakey, SB ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (20) :6046-6047
[2]   Ni-Catalyzed Cross-Coupling of Dimethyl Aryl Amines with Arylboronic Esters under Reductive Conditions [J].
Cao, Zhi-Chao ;
Xie, Si-Jun ;
Fang, Huayi ;
Shi, Zhang-Jie .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (42) :13575-13579
[3]   Direct Borylation of Tertiary Anilines via C-N Bond Activation [J].
Cao, Zhi-Chao ;
Li, Xiao-Lei ;
Luo, Qin-Yu ;
Fang, Huayi ;
Shi, Zhang-Jie .
ORGANIC LETTERS, 2018, 20 (07) :1995-1998
[4]   Low-Valent, High-Spin Chromium-Catalyzed Cleavage of Aromatic Carbon Nitrogen Bonds at Room Temperature: A Combined Experimental and Theoretical Study [J].
Cong, Xuefeng ;
Fan, Fei ;
Ma, Pengchen ;
Luo, Meiming ;
Chen, Hui ;
Zeng, Xiaoming .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (42) :15182-15190
[5]   Biaryl synthesis with arenediazonium salts: cross-coupling, CH-arylation and annulation reactions [J].
Felpin, Francois-Xavier ;
Sengupta, Saumitra .
CHEMICAL SOCIETY REVIEWS, 2019, 48 (04) :1150-1193
[6]   New avenues for C-B bond formation via radical intermediates [J].
Friese, Florian W. ;
Studer, Armido .
CHEMICAL SCIENCE, 2019, 10 (37) :8503-8518
[7]   Recent Methodologies That Exploit Oxidative Addition of C-N Bonds to Transition Metals [J].
Garcia-Carceles, Javier ;
Bahou, Karim A. ;
Bower, John F. .
ACS CATALYSIS, 2020, 10 (21) :12738-12759
[8]  
Hall D, 2011, BORONIC ACIDS, VOL 2: PREPARATION AND APPLICATIONS IN ORGANIC SYNTHESIS, MEDICINE AND MATERIALS, 2ND EDITION, pXV
[9]   Recent Advances in Pyridinium Salts as Radical Reservoirs in Organic Synthesis [J].
He, Fu-Sheng ;
Ye, Shengqing ;
Wu, Jie .
ACS CATALYSIS, 2019, 9 (10) :8943-8960
[10]   Reductive Coupling between C-N and C-O Electrophiles [J].
He, Rong-De ;
Li, Chun-Ling ;
Pan, Qiu-Quan ;
Guo, Peng ;
Liu, Xue-Yuan ;
Shu, Xing-Zhong .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (32) :12481-12486