Palladium-catalyzed synthesis of N-arylated carbazoles using anilines and cyclic diaryliodonium salts

被引：62

作者：

Riedmueller, Stefan ^{[1
,2
]}

Nachtsheim, Boris J. ^{[2
]}

机构：

[1] Merck KGaA, Performance Mat Div, D-64293 Darmstadt, Germany

[2] Univ Tubingen, Inst Organ Chem, D-72076 Tubingen, Germany

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 9卷

关键词：

amination; carbazoles; hypervalent; iodine; iodonium salts; LIGHT-EMITTING-DIODES; ONE-POT SYNTHESIS; PRIMARY AMINES; DIARYLBROMONIUM SALTS; SELECTIVE ARYLATION; OXIDATIVE AMINATION; COUPLING REACTIONS; HOST MATERIALS; EFFICIENT; IODINE;

D O I：

10.3762/bjoc.9.136

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The direct synthesis of N-arylated carbazoles through a palladium-catalyzed amination of cyclic iodonium salts with anilines is described. In particular, electron-poor aniline derivatives reacted smoothly with only 5 mol % of Pd(OAc)(2) as catalyst to give the desired products in up to 71% yield. Furthermore, the reactivity of cyclic iodonium salts is compared with the reactivity of the corresponding cyclic bromonium analogues.

引用

页码：1202 / 1209

页数：8

共 44 条

[1]

[Anonymous], 2003, ANGEW CHEM, DOI DOI 10.1002/ANGE.200250648

[2]

Beletskaya IP, 1998, TETRAHEDRON LETT, V39, P5621, DOI 10.1016/S0040-4039(98)01063-6

[3] Palladium- and copper-catalyzed selective arylation of 5-aryltetrazoles by diaryliodonium salts [J].

Beletskaya, IP ;

Davydov, DV ;

Gorovoy, MS .

TETRAHEDRON LETTERS, 2002, 43 (35) :6221-6223

[4] ELECTROPHILIC AND HOMOLYTIC CLEAVAGE OF 5-ARYL-5H-DIBENZIODOLES [J].

BERINGER, FM ;

CHANG, LL .

JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (26) :4055-&

[5] DIARYLIODONIUM SALTS .23. COMPETITIVE ARYLATION OF NUCLEOPHILES + REDUCTANTS BY SUBSTITUTED DIPHENYLIODONIUM CATIONS [J].

BERINGER, FM ;

FALK, RA .

JOURNAL OF THE CHEMICAL SOCIETY, 1964, (NOV) :4442-&

[6] Efficient and general one-pot synthesis of diaryliodonium triflates: Optimization, scope and limitations [J].

Bielawski, Marcin ;

Zhu, Mingzhao ;

Olofsson, Berit .

ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (17-18) :2610-2618

[7] High-yielding one-pot synthesis of diaryliodonium triflates from arenes and iodine or aryl iodides [J].

Bielawski, Marcin ;

Olofsson, Berit .

CHEMICAL COMMUNICATIONS, 2007, (24) :2521-2523

[8] Regioselective arylation of N-tributylstannylated 5-substituted tetrazoles by diaryliodonium salts in the presence of Cu(OAc)2 [J].

Davydov, DV ;

Beletskaya, IP ;

Semenov, BB ;

Smushkevich, YI .

TETRAHEDRON LETTERS, 2002, 43 (35) :6217-6219

[9] Solution processable small molecules for organic light-emitting diodes [J].

Duan, Lian ;

Hou, Liudong ;

Lee, Tae-Woo ;

Qiao, Juan ;

Zhang, Deqiang ;

Dong, Guifang ;

Wang, Liduo ;

Qiu, Yong .

JOURNAL OF MATERIALS CHEMISTRY, 2010, 20 (31) :6392-6407

[10]

Farooq U., 2009, ANGEW CHEM, V121, P1036, DOI DOI 10.1002/ANGE.200805027

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