Rhodium-Catalyzed Intramolecular Difluoromethylenative Dearomatization of Phenols

被引：28

作者：

Li, Yajun ^{[1
,2
]}

Zhang, Lisi ^{[1
]}

Zhang, Li ^{[1
,3
]}

Wu, Yongming ^{[1
]}

Gong, Yuefa ^{[2
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China

[2] Huazhong Univ Sci & Technol, Sch Chem & Chem Engn, Wuhan 430074, Peoples R China

[3] Shanghai Univ, Sch Sci, Dept Chem, Shanghai 200444, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 35期

基金：

中国国家自然科学基金;

关键词：

Homogeneous catalysis; Spiro compounds; Fluorine; Rhodium; Phenols; PALLADIUM(0)-CATALYZED ARYLATIVE DEAROMATIZATION; ALPHA; BETA-UNSATURATED CARBOXYLIC-ACIDS; COPPER-MEDIATED DIFLUOROMETHYLATION; CRAFTS ALLYLIC ALKYLATION; NUCLEOPHILIC DIFLUOROMETHYLATION; ASYMMETRIC DEAROMATIZATION; OXIDATIVE DEAROMATIZATION; EFFICIENT SYNTHESIS; ENANTIOSELECTIVE CONSTRUCTION; POLYSUBSTITUTED FURANS;

D O I：

10.1002/ejoc.201301225

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rhodium-catalyzed intramolecular difluoromethylenative dearomatization of phenols to yield azaspirocyclohexadienones containing all-carbon quaternary centers in good to excellent yields was developed. A variety of functional groups proved compatible with the transformation. This method could also be used for difluoromethylenative dearomatization of indoles. Preliminary mechanism studies suggest that a pure radical mechanism is not involved in this reaction.

引用

页码：8039 / 8047

页数：9

共 117 条

[1]

[Anonymous], ANGEW CHEM

[2]

[Anonymous], 2013, ANGEW CHEM-GER EDIT, V125, P2146, DOI DOI 10.1002/ANGE.201209250

[3]

[Anonymous], ANGEW CHEM

[4] Remarkably reactive dihydroindoloindoles via palladium-catalysed dearomatisation [J].

Bedford, Robin B. ;

Fey, Natalie ;

Haddow, Mairi F. ;

Sankey, Rosalind F. .

CHEMICAL COMMUNICATIONS, 2011, 47 (12) :3649-3651

[5] Reactive 4a-alkyl-4aH-carbazoles by catalytic dearomatisation, and their unusual dimerisation and dealkylation reactions [J].

Bedford, Robin B. ;

Butts, Craig P. ;

Haddow, Mairi F. ;

Osborne, Robert ;

Sankey, Rosalind F. .

CHEMICAL COMMUNICATIONS, 2009, (32) :4832-4834

[6] Synthesis and reactivity of halogeno-difluoromethyl aromatics and heterocycles -: Application to the synthesis of gem-difluorinated bioactive compounds [J].

Burkholder, CR ;

Dolbier, WR ;

Médebielle, M .

JOURNAL OF FLUORINE CHEMISTRY, 2001, 109 (01) :39-48

[7] The syntheses of nonnucleoside, HIV-1 reverse transcriptase inhibitors containing a CF2 group -: The SRN1 reactions of 2-(bromodifluoromethyl)benzoxazole with the anions derived from heterocyclic thiols and phenolic compounds [J].

Burkholder, CR ;

Dolbier, WR ;

Médebielle, M .

JOURNAL OF FLUORINE CHEMISTRY, 2000, 102 (1-2) :369-376

[8] Enantioselective Gold-Catalyzed Synthesis of Polycyclic Indolines [J].

Cera, Gianpiero ;

Chiarucci, Michel ;

Mazzanti, Andrea ;

Mancinelli, Michele ;

Bandini, Marco .

ORGANIC LETTERS, 2012, 14 (05) :1350-1353

[9] Copper-Catalyzed Synthesis of Azaspirocyclohexadienones from α-Azido-N-arylamides under an Oxygen Atmosphere [J].

Chiba, Shunsuke ;

Zhang, Line ;

Lee, Jian-Yuan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (21) :7266-+

[10] Recent Advances in Phenol Dearomatization and Its Application in Complex Syntheses [J].

Ding, Qiuping ;

Ye, Yang ;

Fan, Renhua .

SYNTHESIS-STUTTGART, 2013, 45 (01) :1-16

← 1 2 3 4 5 6 7 8 9 10 →