Regioselective functionalization of unreactive carbon-hydrogen bonds

被引：244

作者：

Daugulis, Olafs ^{[1
]}

Zaitsev, Vladimir G. ^{[1
]}

Shabashov, Dmitry ^{[1
]}

Pham, Quynh-Nhu ^{[1
]}

Lazareva, Anna ^{[1
]}

机构：

[1] Univ Houston, Dept Chem, Houston, TX 77204 USA

来源：

SYNLETT | 2006年 / 20期

关键词：

arylations; C-H activation; catalysis; cross-coupling; palladium;

D O I：

10.1055/s-2006-956468

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and general method for arylation of carbon-bydrogen bonds in compounds containing directing groups has been developed. Anilides, benzylamines, benzoic acids, 2-aryl and alkylpyridines can be arylated in ortho-positions by using a combination of substrate, aryl iodide, silver acetate and catalytic palladium acetate. The use of a pyridine-containing removable auxiliary ligand allows the arylation of beta-positions in carboxylic acid derivatives and gamma-positions in amine derivatives. Non-activated sp(3) carbon-hydrogen bonds are also reactive. A mechanistically distinct method for the alkenylation of anilides has also been developed. 1 Introduction 2 Concept Development and Initial Results 3 Expansion of Arylation Scope 4 Conclusion and Outlook

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收藏

页码：3382 / 3388

页数：7

相关论文

共 57 条

[1] Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure [J].

Barder, TE ;

Walker, SD ;

Martinelli, JR ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4685-4696

[2] The catalytic intermolecular orthoarylation of phenols [J].

Bedford, RB ;

Coles, SJ ;

Hursthouse, MB ;

Limmert, ME .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (01) :112-114

[3] Selective Pd-catalyzed oxidative coupling of anilides with olefins through C-H bond activation at room temperature [J].

Boele, MDK ;

van Strijdonck, GPF ;

de Vries, AHM ;

Kamer, PCJ ;

de Vries, JG ;

van Leeuwen, PWNM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (08) :1586-1587

[4] Biaryl synthesis via direct arylation: Establishment of an efficient catalyst for intramolecular processes [J].

Campeau, LC ;

Parisien, M ;

Leblanc, M ;

Fagnou, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (30) :9186-9187

[5] Reactivity of diaryliodine(III) triflates toward palladium(II) and platinum(II):: Reactions of C(sp2)-I bonds to form arylmetal(IV) complexes;: Access to dialkyl(aryl)metal(IV), 1,4-benzenediyl-bridged platinum(IV), and triphenylplatinum(IV) species;: and structural studies of platinum(IV) complexes [J].

Canty, AJ ;

Patel, J ;

Rodemann, T ;

Ryan, JH ;

Skelton, BW ;

White, AH .

ORGANOMETALLICS, 2004, 23 (14) :3466-3473

[6] Thermal, catalytic, regiospecific functionalization of alkanes [J].

Chen, HY ;

Schlecht, S ;

Semple, TC ;

Hartwig, JF .

SCIENCE, 2000, 287 (5460) :1995-1997

[7] Palladium-catalyzed alkylation of aryl C-H bonds with sp3 organotin reagents using benzoquinone as a crucial promoter [J].

Chen, X ;

Li, JJ ;

Hao, XS ;

Goodhue, CE ;

Yu, JQ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (01) :78-79

[8] Palladium-catalyzed alkylation of sp2 and sp3 C-H bonds with methylboroxine and alkylboronic acids:: Two distinct C-H activation pathways [J].

Chen, Xiao ;

Goodhue, Charles E. ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) :12634-12635

[9] Remarkably selective iridium catalysts for the elaboration of aromatic C-H bonds [J].

Cho, JY ;

Tse, MK ;

Holmes, D ;

Maleczka, RE ;

Smith, MR .

SCIENCE, 2002, 295 (5553) :305-308

[10] FORMATION OF COVALENT BONDS FROM PLATINUM OR PALLADIUM TO CARBON BY DIRECT SUBSTITUTION [J].

COPE, AC ;

SIEKMAN, RW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (14) :3272-&

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