Facile N-arylation of amines and sulfonamides and O-arylation of phenols and arenecarboxylic acids

被引：287

作者：

Liu, ZJ ^{[1
]}

Larock, RC ^{[1
]}

机构：

[1] Iowa State Univ, Dept Chem, Ames, IA 50011 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 08期

关键词：

D O I：

10.1021/jo0602221

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

An efficient, transition-metal-free procedure for the N-arylation of amines, sulfonamides, and carbamates and O-arylation of phenols and carboxylic acids has been achieved by allowing these substrates to react with a variety of o-silylaryl triflates in the presence of CsF. Good to excellent yields of arylated products are obtained under very mild reaction conditions. This chemistry readily tolerates a variety of functional groups.

引用

收藏

页码：3198 / 3209

页数：12

相关论文

共 72 条

[1]

[Anonymous], CRC HDB PESTICIDES

[2]

Novel electron-rich bulky phosphine ligands facilitate the palladium-catalyzed preparation of diaryl ethers [J].

Aranyos, A ;

Old, DW ;

Kiyomori, A ;

Wolfe, JP ;

Sadighi, JP ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (18) :4369-4378

[3]

SUBSTITUTED (2-PHENOXYPHENYL)ACETIC ACIDS WITH ANTI-INFLAMMATORY ACTIVITY .2. [J].

ATKINSON, DC ;

GODFREY, KE ;

MYERS, PL ;

PHILLIPS, NC ;

STILLINGS, MR ;

WELBOURN, AP .

JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (10) :1361-1364

[4]

Synthesis of 2,3-dihydroindoles, indoles, and anilines by transition metal-free amination of aryl chlorides [J].

Beller, M ;

Breindl, C ;

Riermeier, TH ;

Tillack, A .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (04) :1403-1412

[5]

Beyer H., 1996, HDB ORGANIC CHEM, P497

[6]

New N- and O-arylations with phenylboronic acids and cupric acetate [J].

Chan, DMT ;

Monaco, KL ;

Wang, RP ;

Winters, MP .

TETRAHEDRON LETTERS, 1998, 39 (19) :2933-2936

[7]

N-arylation of sulfonamidies on solid supports [J].

Combs, AP ;

Rafalski, M .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2000, 2 (01) :29-32

[8]

Czarnik AW, 1996, ACCOUNTS CHEM RES, V29, P112, DOI 10.1021/ar950256n

[9]

Intramolecular O-arylation of phenols with phenylboronic acids: Application to the synthesis of macrocyclic metalloproteinase inhibitors [J].

Decicco, CP ;

Song, Y ;

Evans, DA .

ORGANIC LETTERS, 2001, 3 (07) :1029-1032

[10]

Deng BL, 1999, EUR J ORG CHEM, V1999, P2683

← 1 2 3 4 5 6 7 8 →