Copper-catalyzed Oxidative C-C, C-O, and C-N Bond Forming Reactions of Arylboronic Acids

被引:6
作者
Shirakawa, Eiji [1 ]
Nishikawa, Ryo [1 ]
Uchiyama, Nanase [1 ]
Hata, Ippei [1 ]
Hayashi, Tamio [1 ,2 ]
机构
[1] Kyoto Univ, Dept Chem, Grad Sch Sci, Sakyo Ku, Kyoto 6068502, Japan
[2] Inst Mat Res & Engn, Singapore 117602, Singapore
关键词
CROSS-COUPLING REACTIONS; MANGANESE(III) ACETATE; ORGANOBORON COMPOUNDS; CUPRIC ACETATE; ARYLATION; RADICALS; HETEROCYCLES; DERIVATIVES; BIARYLS;
D O I
10.1246/cl.2013.269
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
CuOTf in combination with PhCO(3)t-Bu as an oxidant was found to catalyze oxidative coupling of arylboronic acids to give stilbenes, aryl benzoates and N-arylimines.
引用
收藏
页码:269 / 271
页数:3
相关论文
共 24 条
[1]   Copper catalyzed allylic oxidation with peresters [J].
Andrus, MB ;
Lashley, JC .
TETRAHEDRON, 2002, 58 (05) :845-866
[2]   New N- and O-arylations with phenylboronic acids and cupric acetate [J].
Chan, DMT ;
Monaco, KL ;
Wang, RP ;
Winters, MP .
TETRAHEDRON LETTERS, 1998, 39 (19) :2933-2936
[3]   Generation of aryl radicals from arylboronic acids by manganese(III) acetate:: Synthesis of biaryls and heterobiaryls [J].
Demir, AS ;
Reis, Ö ;
Emrullahoglu, M .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (02) :578-580
[4]   Potassium permanganate/carboxylic acid/organic solvent: a powerful reagent for enone oxidation and aryl coupling reactions [J].
Demir, Ayhan S. ;
Findik, Hamide .
TETRAHEDRON, 2008, 64 (27) :6196-6201
[5]   Manganese(III) acetate-mediated synthesis of biaryls under microwave irradiation [J].
Demir, Ayhan S. ;
Findik, Hamide ;
Saygili, Nezire ;
Subasi, N. Tuna .
TETRAHEDRON, 2010, 66 (06) :1308-1312
[6]   Radical Addition of Arylboronic Acids to Various Olefins under Oxidative Conditions [J].
Dickschat, Arne ;
Studer, Armido .
ORGANIC LETTERS, 2010, 12 (18) :3972-3974
[7]  
FIESER LF, 1967, REAGENTS ORGANIC SYN, P892
[8]   Practical C-H Functionalization of Quinones with Boronic Acids [J].
Fujiwara, Yuta ;
Domingo, Victoriano ;
Seiple, Ian B. ;
Gianatassio, Ryan ;
Del Bel, Matthew ;
Baran, Phil S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (10) :3292-3295
[9]   Direct C-H Bond Arylation of (Hetero)arenes with Aryl and Heteroarylboronic Acids [J].
Guchhait, Sankar K. ;
Kashyap, Maneesh ;
Saraf, Shuddham .
SYNTHESIS-STUTTGART, 2010, (07) :1166-1170
[10]  
Hall DG, 2005, BORONIC ACIDS: PREPARATION AND APPLICATIONS IN ORGANIC SYNTHESIS AND MEDICINE, P1, DOI 10.1002/3527606548.ch1