Palladium-Catalyzed Synthesis of 2-Substituted Benzothiazoles via a C-H Functionalization/Intramolecular C-S Bond Formation Process

被引：278

作者：

Inamoto, Kiyofumi ^{[1
]}

Hasegawa, Chisa ^{[1
]}

Hiroya, Kou ^{[1
]}

Doi, Takayuki ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Aoba Ku, 6-3 Aoba, Sendai, Miyagi 9808578, Japan

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 22期

基金：

日本学术振兴会;

关键词：

D O I：

10.1021/ol802033p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Catalytic synthesis of 2-substituted benzothiazoles from thiobenzanilides was achieved in the presence of a palladium catalyst through C-H functionalization/C-S bond formation. This method features the use of a novel catalytic system consisting of 10 mol % of Pd(II), 50 mol % of Cu(I), and 2 equiv of Bu4NBr that produced variously substituted benzothiazoles in high yields with good functional group tolerance.

引用

页码：5147 / 5150

页数：4

共 64 条

[1] Assisted ruthenium-catalyzed C-H bond activation: Carboxylic acids as cocatalysts for generally applicable direct arylations in apolar solvents [J].

Ackermann, Lutz ;

Vicente, Ruben ;

Althammer, Andreas .

ORGANIC LETTERS, 2008, 10 (11) :2299-2302

[2] Catalytic arylations with challenging substrates: From air-stable HASPO preligands to indole syntheses and C-H-bond functionalizations [J].

Ackermann, Lutz .

SYNLETT, 2007, (04) :507-526

[3] 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

[4] Synthesis of 2-substituted-benzothiazoles by palladium-catalyzed intramolecular cyclization of o-bromophenylthioureas and o-bromophenylthioamides [J].

Benedí, C ;

Bravo, F ;

Uriz, P ;

Fernández, E ;

Claver, C ;

Castillón, S .

TETRAHEDRON LETTERS, 2003, 44 (32) :6073-6077

[5] Hypervalent iodine mediated intramolecular cyclization of thioformanilides: Expeditious approach to 2-substituted benzothiazoles [J].

Bose, D. Subhas ;

Idrees, Mohd. .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (21) :8261-8263

[6] Synthesis of 2-arylbenzothiazoles by DDQ-promoted cyclization of thioformanilides; A solution-phase strategy for library synthesis [J].

Bose, D. Sublias ;

Idrees, Mohd. ;

Srikanth, Bingi .

SYNTHESIS-STUTTGART, 2007, (06) :819-823

[7] Twofold C-H functionalization:: Palladium-catalyzed ortho arylation of anilides [J].

Brasche, Gordon ;

Garcia-Fortanet, Jorge ;

Buchwald, Stephen L. .

ORGANIC LETTERS, 2008, 10 (11) :2207-2210

[8] C-H functionalization/C-N bond formation: Copper-catalyzed synthesis of benzimidazoles from amidines [J].

Brasche, Gordon ;

Buchwald, Stephen L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (10) :1932-1934

[9] A solution to the 2-pyridyl organometallic cross-coupling problem:: Regioselective catalytic direct arylation of pyridine N-oxides [J].

Campeau, LC ;

Rousseaux, S ;

Fagnou, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (51) :18020-18021

[10] Site-selective Sp2 and benzylic Sp3 palladium-catalyzed direct arylation [J].

Campeau, Louis-Charles ;

Schipper, Derek J. ;

Fagnou, Keith .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (11) :3266-+

← 1 2 3 4 5 6 7 →