Ruthenium- and palladium-catalyzed consecutive coupling and cyclization of aromatic sulfoximines with phenylboronic acids: an efficient route to dibenzothiazines

被引：70

作者：

Chinnagolla, Ravi Kiran ^{[1
]}

Vijeta, Arjun ^{[1
]}

Jeganmohan, Masilamani ^{[1
]}

机构：

[1] Indian Inst Sci Educ & Res, Dept Chem, Pune 411021, Maharashtra, India

来源：

CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 65期

关键词：

H BOND ACTIVATION; ASYMMETRIC-SYNTHESIS; N-METHOXYBENZAMIDES; DIRECT ARYLATION; BORONIC ACIDS; ONE-POT; BENZOTHIAZINES; KETONES; FUNCTIONALIZATION; ANNULATION;

D O I：

10.1039/c5cc04589d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A ruthenium-catalyzed ortho arylation of aromatic sulfoximines with aromatic boronic acids followed by intramolecular cyclization in the presence of a palladium catalyst, providing dibenzothiazine derivatives in two consecutive steps, is described.

引用

页码：12992 / 12995

页数：4

共 57 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] 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

[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] C-H Bond Functionalization in Water Catalyzed by Carboxylato Ruthenium(II) Systems [J].

Arockiam, Percia B. ;

Fischmeister, Cedric ;

Bruneau, Christian ;

Dixneuf, Pierre H. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (37) :6629-6632

[5]

Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153j, 10.1021/cr300153J]

[6] Ru(II)-catalyzed intermolecular ortho-C-H amidation of aromatic ketones with sulfonyl azides [J].

Bhanuchandra, M. ;

Yadav, M. Ramu ;

Rit, Raja K. ;

Kuram, Malleswara Rao ;

Sahoo, Akhila K. .

CHEMICAL COMMUNICATIONS, 2013, 49 (45) :5225-5227

[7] An efficient resolution of (+/-)-S-methyl-S-phenylsulfoximine with (+)-10-camphorsulfonic acid by the method of half-quantities [J].

Brandt, J ;

Gais, HJ .

TETRAHEDRON-ASYMMETRY, 1997, 8 (06) :909-912

[8] Highly stereoselective route to dialkyl sulfoxides based upon the sequential displacement of oxygen and carbon leaving groups by Grignard reagents on sulfinyl compounds [J].

Capozzi, MAM ;

Cardellicchio, C ;

Naso, F ;

Spina, G ;

Tortorella, P .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (17) :5933-5936

[9] Syntheses and biological activities of sulfoximine-based acyclic triaryl olefins [J].

Chen, Xiao Yun ;

Park, Seong Jun ;

Buschmann, Helmut ;

De Rosa, Maria ;

Bolm, Carsten .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (13) :4307-4309

[10] A theoretical study on the mechanism, regiochemistry, and stereochemistry of hydrosilylation catalyzed by cationic ruthenium complexes [J].

Chung, LW ;

Wu, YD ;

Trost, BM ;

Ball, ZT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (38) :11578-11582

← 1 2 3 4 5 6 →