Metal-free C-H arylation of aminoheterocycles with arylhydrazines

被引：30

作者：

Taniguchi, Toshihide ^{[1
,3
]}

Imoto, Mitsutaka ^{[1
]}

Takeda, Motonori ^{[1
]}

Matsumoto, Fukashi ^{[2
]}

Nakai, Takeo ^{[2
]}

Mihara, Masatoshi ^{[2
]}

Mizuno, Takumi ^{[2
]}

Nomoto, Akihiro ^{[3
]}

Ogawa, Akiya ^{[3
]}

机构：

[1] Seika Corp, 1-1-82 Kozaika, Wakayama 6410007, Japan

[2] Osaka Municipal Tech Res Inst, Joto Ku, 1-6-50 Morinomiya, Osaka 5368553, Japan

[3] Osaka Prefecture Univ, Grad Sch Engn, Dept Appl Chem, Naka Ku, 1-1 Gakuen Cho, Sakai, Osaka 5998531, Japan

来源：

TETRAHEDRON | 2016年 / 72卷 / 27-28期

关键词：

C-H arylation; Aminoheterocycle; Homolytic aromatic substitution; Arylhydrazine; HOMO energy; PALLADIUM-CATALYZED REACTION; RADICAL ARYLATION; ANILINES; CYCLIZATION; ALDEHYDES; HALIDES; ETHERS;

D O I：

10.1016/j.tet.2016.05.056

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A direct C-H arylation of aminoheterocycles with arylhydrazine hydrochlorides was developed. The reaction proceeds via a homolytic aromatic substitution mechanism involving aryl radicals as the intermediates. The new reaction takes place readily at room temperature in air and in the presence of an inexpensive base. Moreover, the reactivity of this radical arylation correlated with the HOMO energy of aminoheterocycles. This method provides not only a rapid access to diverse arylated heterocycles, but also an atom-efficient alternative to conventional transition-metal-catalyzed cross-coupling between halides and organometallics. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：4132 / 4140

页数：9

共 43 条

[1]

[Anonymous], FREE RADICALS ORGANI

[2] Discovery and Optimization of Selective Nav1.8 Modulator Series That Demonstrate Efficacy in Preclinical Models of Pain [J].

Bagal, Sharan K. ;

Bungay, Peter J. ;

Denton, Stephen M. ;

Gibson, Karl R. ;

Glossop, Melanie S. ;

Hay, Tanya L. ;

Kemp, Mark I. ;

Lane, Charlotte A. L. ;

Lewis, Mark L. ;

Maw, Graham N. ;

Million, William A. ;

Payne, C. Elizabeth ;

Poinsard, Cedric ;

Rawson, David J. ;

Stammen, Blanda L. ;

Stevens, Edward B. ;

Thompson, Lisa R. .

ACS MEDICINAL CHEMISTRY LETTERS, 2015, 6 (06) :650-654

[3]

CHASE BH, 1953, J CHEM SOC, P3549

[4] Phenyl Hydrazine as Initiator for Direct Arene C-H Arylation via Base Promoted Homolytic Aromatic Substitution [J].

Dewanji, Abhishek ;

Murarka, Sandip ;

Curran, Dennis P. ;

Studer, Armido .

ORGANIC LETTERS, 2013, 15 (23) :6102-6105

[5] NEUARTIGE CYANINE .2. NEUARTIGE TRIMETHIN-CYANINE UND EINE SYNTHESE VON 3-AMINO-PYRIDINEN [J].

DICKORE, K ;

KROHNKE, F .

CHEMISCHE BERICHTE-RECUEIL, 1960, 93 (11) :2479-2485

[6] Understanding the reactivity of captodative ethylenes in polar cycloaddition reactions.: A theoretical study [J].

Domingo, Luis R. ;

Chamorro, Eduardo ;

Perez, Patricia .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (12) :4615-4624

[7] How the Structural Elucidation of the Natural Product Stephanosporin Led to New Developments in Aryl Radical and Medicinal Chemistry [J].

Fehler, Stefanie K. ;

Heinrich, Markus R. .

SYNLETT, 2015, 26 (05) :580-603

[8] The synthesis of biaryl compounds by means of the diazo reaction [J].

Gomberg, M ;

Bachmann, WE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1924, 46 :2339-2343

[9] Synthesis of 7-arylquinolinones and 6-arylindoles from 3-aminobiphenyls through regioselective cyclization reactions [J].

Hammer, Sebastian G. ;

Heinrich, Markus R. .

TETRAHEDRON, 2014, 70 (43) :8114-8121

[10]

Harrowven DC, 2004, PROG HET CH, V16, P27

← 1 2 3 4 5 →