Chemoselective Chan-Lam and reductive nitroarene coupling of boronic acid using an octahedral Ni-DMAP complex as catalyst

被引:10
作者
Talukdar, Hrishikesh [1 ]
Gogoi, Daisy [1 ]
Phukan, Prodeep [1 ]
机构
[1] Gauhati Univ, Dept Chem, Gauhati 781014, Assam, India
关键词
Chan -lam reaction; Aniline; Azide; Thiol; Reductive arylation; Nitroarenes; Boronic acid; Nickel catalyst; C-N; ARYLBORONIC ACIDS; ARYL HALIDES; S-ARYLATION; COPPER; EFFICIENT; AMINES; CUI; AMINATION; ANILINES;
D O I
10.1016/j.tet.2023.133251
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An octahedral Ni-DMAP complex has been developed as catalyst for C-N and C-S cross coupling and reductive nitroarene coupling using boronic acid as coupling partner. Reaction of amines, thiols, azides, and tosyl azides with boronic acids could be achieved in presence of 10 mol % of the catalyst in methanol at 80 degrees C without using extra base. The current protocol is highly selective for primary amines in presence of secondary amines, thiols and phenols. Reductive coupling of a range of nitroarenes and boronic acids was also successfully achieved using the same catalyst.(c) 2023 Elsevier Ltd. All rights reserved.
引用
收藏
页数:12
相关论文
共 89 条
[1]   Palladium- and Nickel-Catalyzed Aminations of Aryl Imidazolylsulfonates and Sulfamates [J].
Ackermann, Lutz ;
Sandmann, Rene ;
Song, Weifeng .
ORGANIC LETTERS, 2011, 13 (07) :1784-1786
[2]  
Alfredo Ricci, 2008, AMINO GROUP CHEM SYN
[3]   Aerobic Copper-Catalyzed Organic Reactions [J].
Allen, Scott E. ;
Walvoord, Ryan R. ;
Padilla-Salinas, Rosaura ;
Kozlowski, Marisa C. .
CHEMICAL REVIEWS, 2013, 113 (08) :6234-6458
[4]   Nickel-catalyzed N-arylation of amines with arylboronic acids under open air [J].
Ando, Shin ;
Hirota, Yurina ;
Matsunaga, Hirofumi ;
Ishizuka, Tadao .
TETRAHEDRON LETTERS, 2019, 60 (18) :1277-1280
[5]   Copper-catalyzed coupling of arylboronic acids and amines [J].
Antilla, JC ;
Buchwald, SL .
ORGANIC LETTERS, 2001, 3 (13) :2077-2079
[6]   Triphenylphosphine as reducing agent for copper(II)-catalyzed AGET ATRP [J].
Bai, Liang-jiu ;
Wang, Wen-xiang ;
Wang, Ming-hua ;
Sun, Jin-ming ;
Chen, Hou .
CHINESE JOURNAL OF POLYMER SCIENCE, 2015, 33 (09) :1260-1270
[7]   C-N bond forming cross-coupling reactions: an overview [J].
Bariwal, Jitender ;
Van der Eycken, Erik .
CHEMICAL SOCIETY REVIEWS, 2013, 42 (24) :9283-9303
[8]   Copper-promoted N-cyclopropylation of anilines and amines by cyclopropylboronic acid [J].
Benard, Sebastien ;
Neuville, Luc ;
Zhu, Jieping .
CHEMICAL COMMUNICATIONS, 2010, 46 (19) :3393-3395
[9]   HALO-NITRATO COMPLEXES OF NICKEL(II) AND COPPER(II) [J].
BROWN, DH ;
RICHARDSON, RT .
JOURNAL OF INORGANIC & NUCLEAR CHEMISTRY, 1979, 41 (02) :256-257
[10]   Stereoselective copper-catalyzed Chan-Lam-Evans N-arylation of glucosamines with arylboronic acids at room temperature [J].
Bruneau, Alexandre ;
Brion, Jean-Daniel ;
Alami, Mouad ;
Messaoudi, Samir .
CHEMICAL COMMUNICATIONS, 2013, 49 (75) :8359-8361