Acid Fluorides as Acyl Electrophiles in Suzuki-Miyaura Coupling

被引:59
作者
Ogiwara, Yohei [1 ]
Sakino, Daisuke [1 ]
Sakurai, Yuka [1 ]
Sakai, Norio [1 ]
机构
[1] Tokyo Univ Sci, Fac Sci & Technol, Dept Pure & Appl Chem, Noda, Chiba 2788510, Japan
基金
日本学术振兴会;
关键词
Cross-coupling; Ketones; Acyl fluorides; Boronic acids; Palladium; CATALYZED DIRECT CONVERSION; PREPARING AROMATIC KETONES; ACTIVATED IN-SITU; N-C CLEAVAGE; ARYLBORONIC ACIDS; CARBOXYLIC ANHYDRIDES; BORONIC ACIDS; SODIUM TETRAPHENYLBORATE; ARYL KETONES; CONVENIENT METHOD;
D O I
10.1002/ejoc.201700917
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first palladium-catalyzed construction of ketones through Suzuki-Miyaura reaction by using acid fluorides is described. In contrast to typical acyl electrophiles such as acid chlorides, acid fluorides are uncommon acyl electrophiles to use in boron-based coupling reactions, probably due to a high level of stability toward nucleophiles. This first attempt to use acid fluorides as a coupling partner with boronic acids allowed highly functional group tolerance and a wide substrate scope while affording various ketones in effective yields.
引用
收藏
页码:4324 / 4327
页数:4
相关论文
共 64 条
[1]   Visible Light Photoredox Cross-Coupling of Acyl Chlorides with Potassium Alkoxymethyltrifluoroborates: Synthesis of α-Alkoxyketones [J].
Amani, Javad ;
Sodagar, Esmat ;
Molander, Gary A. .
ORGANIC LETTERS, 2016, 18 (04) :732-735
[2]  
[Anonymous], 2001, ANGEW CHEM
[3]   A rapid, solvent-free, ligandless and mild method for preparing aromatic ketones from acyl chlorides and arylboronic acids via a Suzuki-Miyaura type of coupling reaction [J].
Bandgar, BP ;
Patil, AV .
TETRAHEDRON LETTERS, 2005, 46 (44) :7627-7630
[4]   Palladium-Catalyzed Suzuki-Miyaura Coupling of Aryl Esters [J].
Ben Halima, Taoufik ;
Zhang, Wanying ;
Yalaoui, Imane ;
Hong, Xin ;
Yang, Yun-Fang ;
Houk, Kendall N. ;
Newman, Stephen G. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (03) :1311-1318
[5]   Suzuki-Miyaura Cross-Coupling in Acylation Reactions, Scope and Recent Developments [J].
Blangetti, Marco ;
Rosso, Helena ;
Prandi, Cristina ;
Deagostino, Annamaria ;
Venturello, Paolo .
MOLECULES, 2013, 18 (01) :1188-1213
[6]   Synthesis of unsymmetric ketones via ligandless Pd-catalyzed reaction of acyl chlorides with organoboranes [J].
Bumagin, NA ;
Korolev, DN .
TETRAHEDRON LETTERS, 1999, 40 (15) :3057-3060
[7]   Preparation of acyl fluorides with hydrogen fluoride-pyridine and 1,3-dicyclohexylcarbodiimide [J].
Chen, CP ;
Chien, CT ;
Su, CH .
JOURNAL OF FLUORINE CHEMISTRY, 2002, 115 (01) :75-77
[8]   Nickel-catalyzed cross-coupling of carboxylic anhydrides with arylboronic acids [J].
Chen, Qiang ;
Fan, Xin-Heng ;
Zhang, Li-Peng ;
Yang, Lian-Ming .
RSC ADVANCES, 2014, 4 (96) :53885-53890
[9]  
CHO CS, 1993, J ORGANOMET CHEM, V443, P253
[10]   Palladium-phosphinous acid-catalyzed cross-coupling of aliphatic and aromatic acyl chlorides with boronic acids [J].
Ekoue-Kovi, Kekeli ;
Xu, Hanhui ;
Wolf, Christian .
TETRAHEDRON LETTERS, 2008, 49 (40) :5773-5776