Selective O-Difluoromethylation of 1,3-Diones by Bromodifluoromethylating Reagents

被引:54
作者
Liu, Guokai [1 ]
Wang, Xin [1 ]
Xu, Xiu-Hua [1 ]
Lu, Xu [1 ]
Tokunaga, Etsuko [1 ]
Tsuzuki, Seiji
Shibata, Norio [1 ]
机构
[1] Nagoya Inst Technol, Dept Frontier Mat, Grad Sch Engn, Showa Ku, Nagoya, Aichi, Japan
关键词
PHENYL SULFONE; EFFICIENT SYNTHESIS; TRIFLUOROMETHYLATION; DIFLUOROCARBENE; FACILE; (PHENYLSULFONYL)DIFLUOROMETHYLATION; FLUOROALKYLATION; ROUTE; SALTS; ACID;
D O I
10.1021/ol4000313
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The regioselective Odifluoromethylation of 1,3-diones was achieved via in situ generation of difluorocarbene from bromodifluoromethylating reagents in the presence of an organic base. A wide variety of difluormethyl enol ethers were obtained in good to excellent yields. The reaction mechanism is discussed based on ab initio calculations (kcal/mol).
引用
收藏
页码:1044 / 1047
页数:4
相关论文
共 56 条
[1]   The Productive Merger of Iodonium Salts and Organocatalysis: A Non-photolytic Approach to the Enantioselective α-Trifluoromethylation of Aldehydes [J].
Allen, Anna E. ;
MacMillan, David W. C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (14) :4986-+
[2]   Facile one-pot synthesis of N-difluoromethyl-2-pyridone derivatives [J].
Ando, Makoto ;
Wada, Toshihiro ;
Sato, Nagaaki .
ORGANIC LETTERS, 2006, 8 (17) :3805-3808
[3]  
[Anonymous], 2008, BIOORGAN MED CHEM
[4]   A FACILE, GENERAL-ROUTE TO PERFLUOROALKYL ALLENES [J].
BURTON, DJ ;
HARTGRAVES, GA ;
HSU, J .
TETRAHEDRON LETTERS, 1990, 31 (26) :3699-3702
[5]   A new synthesis of 2-fluoro-1-naphthols [J].
Cai, XH ;
Wu, K ;
Dolbier, WR .
JOURNAL OF FLUORINE CHEMISTRY, 2005, 126 (04) :479-482
[6]   DIFLUOROIODOMETHANE - PRACTICAL SYNTHESIS AND REACTION WITH ALKENES [J].
CAO, P ;
DUAN, JX ;
CHEN, QY .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (06) :737-738
[7]   A SIMPLE CONVENIENT METHOD FOR PREPARATION OF DIFLUOROMETHYL ETHERS USING FLUOROSULFONYLDIFLUORACETIC ACID AS A DIFLUOROCARBENE PRECURSOR [J].
CHEN, QY ;
WU, SW .
JOURNAL OF FLUORINE CHEMISTRY, 1989, 44 (03) :433-440
[8]   Highly Enantioselective Copper-Catalyzed Electrophilic Trifluoromethylation of β-Ketoesters [J].
Deng, Qing-Hai ;
Wadepohl, Hubert ;
Gade, Lutz H. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (26) :10769-10772
[9]   HYDROGEN-BOND DONOR PROPERTIES OF THE DIFLUOROMETHYL GROUP [J].
ERICKSON, JA ;
MCLOUGHLIN, JI .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (06) :1626-1631
[10]  
Frisch M., 2004, GAUSSIAN 03 REVISION, DOI DOI 10.1016/J.MOLSTRUC.2017.03.014