LDA-Mediated Synthesis of Triarylmethanes by Arylation of Diarylmethanes with Fluoroarenes at Room Temperature

被引：57

作者：

Ji, Xinfei ^{[1
]}

Huang, Tao ^{[1
]}

Wu, Wei ^{[1
]}

Liang, Fang ^{[1
]}

Cao, Song ^{[1
]}

机构：

[1] E China Univ Sci & Technol, Sch Pharm, Shanghai Key Lab Chem Biol, Shanghai 200237, Peoples R China

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 20期

基金：

中国国家自然科学基金;

关键词：

C-H BOND; CROSS-COUPLING REACTIONS; GEM-DIFLUOROALKENES; F ACTIVATION; POLYFLUOROARENES; CYCLIZATION; ACCESS; ALKYLATION; FUNCTIONALIZATION; REGIOSELECTIVITY;

D O I：

10.1021/acs.orglett.5b02602

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical and convenient approach for the secondary C(sp(3))-H arylation of diarylmethanes with various fluoroarenes is described. The reaction proceeds smoothly in the presence of LDA (lithium diisopropylamide) at room temperature and affords triarylmethanes in moderate to high yields.

引用

页码：5096 / 5099

页数：4

共 68 条

[1] Efficient aryl-(hetero)aryl coupling by activation of C-Cl and C-F bonds using nickel complexes of air-stable phosphine oxides [J].

Ackermann, L ;

Born, R ;

Spatz, JH ;

Meyer, D .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (44) :7216-7219

[2] Functionalization of Fluorinated Molecules by Transition-Metal-Mediated C-F Bond Activation To Access Fluorinated Building Blocks [J].

Ahrens, Theresia ;

Kohlmann, Johannes ;

Ahrens, Mike ;

Braun, Thomas .

CHEMICAL REVIEWS, 2015, 115 (02) :931-972

[3] C-F Bond Activation in Organic Synthesis [J].

Amii, Hideki ;

Uneyama, Kenji .

CHEMICAL REVIEWS, 2009, 109 (05) :2119-2183

[4] Generation and cyclization of a benzyne-tethered alkyllithium: Preparation of 4-substituted indans [J].

Bailey, WF ;

Longstaff, SC .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (03) :432-433

[5]

Barluenga J, 2002, CHEM-EUR J, V8, P2034, DOI 10.1002/1521-3765(20020503)8:9<2034::AID-CHEM2034>3.0.CO

[6]

2-I

[7] ABINITIO CALCULATIONS ON N-METHYLMETHANESULFONAMIDE AND METHYL METHANESULFONATE FOR THE DEVELOPMENT OF FORCE-FIELD TORSIONAL PARAMETERS AND THEIR USE IN THE CONFORMATIONAL-ANALYSIS OF SOME NOVEL ESTROGENS [J].

BINDAL, RD ;

GOLAB, JT ;

KATZENELLENBOGEN, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (22) :7861-7868

[8] An Alternative Role for Acetylenes: Activation of Fluorobenzenes toward Nucleophilic Aromatic Substitution [J].

Bizier, Nicholas P. ;

Wackerly, Jay Wm. ;

Braunstein, Eric D. ;

Zhang, Mengfei ;

Nodder, Stephen T. ;

Carlin, Stephen M. ;

Katz, Jeffrey L. .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (12) :5987-5998

[9]

BURMESTER A, 1981, SYNTHESIS-STUTTGART, P125

[10] Preparation of tertiary benzylic nitriles from aryl fluorides [J].

Caron, S ;

Vazquez, E ;

Wojcik, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (04) :712-713

← 1 2 3 4 5 6 7 →