Synthesis of Novel Aryl and Heteroaryl Acyl Sulfonimidamides via Pd-Catalyzed Carbonylation Using a Nongaseous Precursor

被引:46
作者
Borhade, Sanjay R. [1 ]
Sandstrom, Anja [1 ]
Arvidsson, Per I. [1 ]
机构
[1] Uppsala Univ, Dept Med Chem BMC, SE-75123 Uppsala, Sweden
关键词
PROTEASE INHIBITORS; EX-SITU; BIOISOSTERES; SULFONAMIDES; ARYLATION;
D O I
10.1021/ol400049m
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Hitherto unexplored aryl and heteroaryl acyl sulfonimidamides have been prepared through the development of a new Pd-catalyzed carbonylation protocol. This novel methodology, employing sulfonimidamides as nucleophiles and CO gas ex situ released from solid Mo(CO)(6) in a sealed two-chamber system, yields a wide range of carbamate protected acyl sulfonimidamides in good to excellent yields.
引用
收藏
页码:1056 / 1059
页数:4
相关论文
共 45 条
[1]   Copper-Catalyzed N-Arylation of Sulfonimidamides [J].
Azzaro, Stephane ;
Desage-El Murr, Marine ;
Fensterbank, Louis ;
Lacote, Emmanuel ;
Malacria, Max .
SYNLETT, 2011, (06) :849-851
[2]   Palladium-Catalyzed Carbonylation-A Reaction Come of Age [J].
Barnard, Christopher F. J. .
ORGANOMETALLICS, 2008, 27 (21) :5402-5422
[3]   PROGRESS IN HYDROFORMYLATION AND CARBONYLATION [J].
BELLER, M ;
CORNILS, B ;
FROHNING, CD ;
KOHLPAINTNER, CW .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1995, 104 (01) :17-85
[4]   Hepatitis C virus NS3 protease inhibitors: Large, flexible molecules of peptide origin show satisfactory permeability across Caco-2 cells [J].
Bergstrom, Christel A. S. ;
Bolin, Sara ;
Artursson, Per ;
Ronn, Robert ;
Sandstrom, Anja .
EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES, 2009, 38 (05) :556-563
[5]   Palladium-Catalyzed Carbonylation Reactions of Aryl Halides and Related Compounds [J].
Brennfuehrer, Anne ;
Neumann, Helfried ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (23) :4114-4133
[6]   Enantiopure sulfoxides: recent applications in asymmetric synthesis [J].
Carmen Carreno, M. ;
Hernandez-Torres, Gloria ;
Ribagorda, Maria ;
Urbano, Antonio .
CHEMICAL COMMUNICATIONS, 2009, (41) :6129-6144
[7]   Catalytic C-H amination: recent progress and future directions [J].
Collet, Florence ;
Dodd, Robert H. ;
Dauban, Philippe .
CHEMICAL COMMUNICATIONS, 2009, (34) :5061-5074
[8]  
CONDROSKI KR, 2006, DIS WEEK MAY 20 25 L
[9]   Sulfonimidamides: Efficient chiral iminoiodane precursors for diastereoselective copper-catalyzed aziridination of olefins [J].
Di Chenna, PH ;
Robert-Peillard, F ;
Dauban, P ;
Dodd, RH .
ORGANIC LETTERS, 2004, 6 (24) :4503-4505
[10]   Silacarboxylic Acids as Efficient Carbon Monoxide Releasing Molecules: Synthesis and Application in Palladium-Catalyzed Carbonylation Reactions [J].
Friis, Stig D. ;
Taaning, Rolf H. ;
Lindhardt, Anders T. ;
Skrydstrup, Troels .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (45) :18114-18117