Direct S-Arylation of Unactivated Arylsulfoxides Using [Pd(IPr*)(cin)Cl]

The direct S-arylation of unactivated arylsulfoxides catalyzed by [Pd(IPr*)(cin)Cl] is described. Several arylmethylsulfoxides were coupled to various aryl halides in moderate to good yields (17 examples, 34–85%). Scope, limitations, and reaction mechanism are discussed.

[1]  P. Walsh,et al.  Palladium-catalyzed direct arylation of methyl sulfoxides with aryl halides. , 2013, Journal of the American Chemical Society.

[2]  S. Nolan,et al.  Solvent-free aryl amination catalysed by [Pd(NHC)] complexes , 2013 .

[3]  A. Slawin,et al.  Extending the utility of [Pd(NHC)(cinnamyl)Cl] precatalysts: Direct arylation of heterocycles , 2012, Beilstein journal of organic chemistry.

[4]  S. Nolan,et al.  An Efficient Palladium‐NHC (NHC=N‐Heterocyclic Carbene) and Aryl Amination Pre‐Catalyst: [Pd(IPr*)(cinnamyl)Cl] , 2012 .

[5]  A. Slawin,et al.  [Pd(IPr*)(cinnamyl)Cl]: an efficient pre-catalyst for the preparation of tetra-ortho-substituted biaryls by Suzuki-Miyaura cross-coupling. , 2012, Chemistry.

[6]  Ka Hou Hoi,et al.  The development of bulky palladium NHC complexes for the most-challenging cross-coupling reactions. , 2012, Angewandte Chemie.

[7]  A. Stepan,et al.  Sequential allylic C-H amination/vinylic C-H arylation: a strategy for unnatural amino acid synthesis from α-olefins. , 2012, Organic letters.

[8]  S. Nolan,et al.  N-Heterocyclic carbene (NHC) ligands and palladium in homogeneous cross-coupling catalysis: a perfect union. , 2011, Chemical Society reviews.

[9]  A. Spek,et al.  IPr* an easily accessible highly hindered N-heterocyclic carbene. , 2010, Dalton transactions.

[10]  X. Bantreil,et al.  Aryl sulfoxides from allyl sulfoxides via [2,3]-sigmatropic rearrangement and domino Pd-catalyzed generation/arylation of sulfenate anions. , 2010, Organic letters.

[11]  S. Nolan,et al.  Well-defined N-heterocyclic carbenes-palladium(II) precatalysts for cross-coupling reactions. , 2008, Accounts of chemical research.

[12]  X. Luan,et al.  A chiral bis-sulfoxide ligand in late-transition metal catalysis; rhodium-catalyzed asymmetric addition of arylboronic acids to electron-deficient olefins. , 2008, Journal of the American Chemical Society.

[13]  G. Poli,et al.  Enantioselective synthesis of aryl sulfoxides via palladium-catalyzed arylation of sulfenate anions. , 2007, Organic letters.

[14]  M. Mellah,et al.  Chiral sulfur ligands for asymmetric catalysis. , 2007, Chemical reviews.

[15]  F. Colobert,et al.  Efficient palladium catalyzed synthesis of heteroaromatic sulfoxides , 2007 .

[16]  G. Poli,et al.  Aryl sulfoxides via palladium-catalyzed arylation of sulfenate anions. , 2006, Organic letters.

[17]  G. Poli,et al.  Preparation of allyl sulfoxides by palladium-catalyzed allylic alkylation of sulfenate anions. , 2006, The Journal of organic chemistry.

[18]  Nicolas Marion,et al.  (IPr)Pd(acac)Cl: an easily synthesized, efficient, and versatile precatalyst for C-N and C-C bond formation. , 2006, The Journal of organic chemistry.

[19]  Jianguo Mei,et al.  Modified (NHC)Pd(allyl)Cl (NHC = N-heterocyclic carbene) complexes for room-temperature Suzuki-Miyaura and Buchwald-Hartwig reactions. , 2006, Journal of the American Chemical Society.

[20]  R. Bentley Role of sulfur chirality in the chemical processes of biology. , 2005, Chemical Society reviews.

[21]  R. Vilar,et al.  Monoligated palladium species as catalysts in cross-coupling reactions. , 2005, Angewandte Chemie.

[22]  F. Diederich,et al.  Book review: Metal-catalyzed cross-coupling reactions. F. Diederich and P. J. Stang (eds) Wiley–VCH, Weinheim, 1998. xxi + 517 pages, £85 ISBN 3–527–29421–X , 1998 .

[23]  F. Glorius,et al.  An N-heterocyclic carbene ligand with flexible steric bulk allows Suzuki cross-coupling of sterically hindered aryl chlorides at room temperature. , 2003, Angewandte Chemie.

[24]  J. Hartwig,et al.  Palladium-Catalyzed α-Arylation of Carbonyl Compounds and Nitriles , 2003 .

[25]  S. Nolan,et al.  Well-defined, air-stable (NHC)Pd(Allyl)Cl (NHC = N-heterocyclic carbene) catalysts for the arylation of ketones. , 2002, Organic letters.

[26]  S. Buchwald,et al.  Palladium-Catalyzed α-Arylation of Ketones , 1997 .

[27]  M. C. Carreño,et al.  Applications of Sulfoxides to Asymmetric Synthesis of Biologically Active Compounds , 1995 .

[28]  C. Bolm,et al.  Applications of Catalytic Asymmetric Sulfide Oxidations to the Syntheses of Biologically Active Sulfoxides , 2005 .