Palladium-Catalyzed Direct Arylation of Selenophene

被引：45

作者：

Rampon, Daniel S. ^{[1
,2
]}

Wessjohann, Ludger A. ^{[2
]}

Schneider, Paulo H. ^{[1
]}

机构：

[1] Univ Fed Rio Grande do Sul, Inst Quim, Dept Quim Organ, BR-91501970 Porto Alegre, RS, Brazil

[2] Leibniz Inst Plant Biochem, Dept Bioorgan Chem, D-06120 Halle, Saale, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 13期

关键词：

CROSS-COUPLING REACTIONS; ZEROVALENT PALLADIUM; OXIDATIVE ADDITION; BOND FORMATION; ARYL BROMIDES; THIOPHENE; FUNCTIONALIZATION; REACTIVITY; MECHANISM; (HETERO)ARENES;

D O I：

10.1021/jo500094t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and convenient method was developed for the regioselective formation of 2-aryl- or 2,5-diarylselenophenes via a palladium-catalyzed direct arylation. This protocol is suitable for a wide range of aryl halides containing different functional groups. The 2-arylated substrates can undergo an additional regioselective direct arylation event furnishing symmetrical or unsymmetrical 2,5-diaryl selenophenes in good yield. Competition experiments and the role of the acid additive are in agreement with a concerted metalation deprotonation (CMD) pathway.

引用

页码：5987 / 5992

页数：6

共 91 条

[1] Direct synthesis of sensitive selenocysteine peptides by the Ugi reaction [J].

Abbas, Muhammad ;

Wessjohann, Ludger A. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (47) :9330-9333

[2] Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].

Ackermann, Lutz .

CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345

[3] Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].

Ackermann, Lutz ;

Vicente, Ruben ;

Kapdi, Anant R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826

[4] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].

Alberico, Dino ;

Scott, Mark E. ;

Lautens, Mark .

CHEMICAL REVIEWS, 2007, 107 (01) :174-238

[5] Selenophene vs. thiophene in benzothiadiazole-based low energy gap donor-acceptor polymers for photovoltaic applications [J].

Alghamdi, Abdulaziz A. B. ;

Watters, Darren C. ;

Yi, Hunan ;

Al-Faifi, Solyman ;

Almeataq, Mohammed S. ;

Coles, David ;

Kingsley, James ;

Lidzey, David G. ;

Iraqi, Ahmed .

JOURNAL OF MATERIALS CHEMISTRY A, 2013, 1 (16) :5165-5171

[6] ROLE AND EFFECTS OF HALIDE-IONS ON THE RATES AND MECHANISMS OF OXIDATIVE ADDITION OF IODOBENZENE TO LOW-LIGATED ZEROVALENT PALLADIUM COMPLEXES PD0(PPH3)2 [J].

AMATORE, C ;

AZZABI, M ;

JUTAND, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (22) :8375-8384

[7] MECHANISM OF OXIDATIVE ADDITION OF PALLADIUM(0) WITH AROMATIC IODIDES IN TOLUENE, MONITORED AT ULTRAMICROELECTRODES [J].

AMATORE, C ;

PFLUGER, F .

ORGANOMETALLICS, 1990, 9 (08) :2276-2282

[8] RATES AND MECHANISM OF THE FORMATION OF ZEROVALENT PALLADIUM COMPLEXES FROM MIXTURES OF PD(OAC)(2) AND TERTIARY PHOSPHINES AND THEIR REACTIVITY IN OXIDATIVE ADDITIONS [J].

AMATORE, C ;

CARRE, E ;

JUTAND, A ;

MBARKI, MA .

ORGANOMETALLICS, 1995, 14 (04) :1818-1826

[9] Anionic Pd(0) and Pd(II) intermediates in palladium-catalyzed Heck and cross-coupling reactions [J].

Amatore, C ;

Jutand, A .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (05) :314-321

[10]

Arena G., 1993, J CHEM SOC PERK T, V2, P1941

← 1 2 3 4 5 6 7 8 9 10 →