Synthesis of dienyl ketones via palladium(II)-catalyzed direct cross-coupling reactions between simple alkenes and vinyl ketones: application to the synthesis of vitamin A1 and bornelone.

An efficient and general method for the synthesis of conjugated dienyl ketones via palladium(II) acetate catalyzed direct cross-coupling between simple alkenes and vinyl ketones is reported. This method has been successfully applied for the synthesis of Vitamin A1 and bornelone.

[1]  Zhong-Quan Liu,et al.  Transition metal-catalyzed C(vinyl)-C(vinyl) bond formation via double C(vinyl)-H bond activation. , 2013, Chemical Society reviews.

[2]  T. Loh,et al.  Ruthenium- and rhodium-catalyzed cross-coupling reaction of acrylamides with alkenes: efficient access to (Z,E)-dienamides. , 2012, Chemical communications.

[3]  J. Bergueiro,et al.  Cross-coupling reactions of organosilicon compounds in the stereocontrolled synthesis of retinoids. , 2012, Chemistry.

[4]  A. Lera,et al.  Synthesis of C40‐Symmetrical Fully Conjugated Carotenoids by Olefin Metathesis , 2011 .

[5]  L. Brown,et al.  Syntheses of 13C2-labelled 11Z-retinals , 2011 .

[6]  T. Loh,et al.  Synthesis and characterization of a cyclic vinylpalladium( ii ) complex: vinylpalladium species as the possible intermediate in the catalytic direct olefination reaction of enamide , 2011 .

[7]  E. Negishi,et al.  Highly selective synthesis of conjugated dienoic and trienoic esters via alkyne elementometalation–Pd-catalyzed cross-coupling , 2011, Proceedings of the National Academy of Sciences.

[8]  F. Glorius,et al.  Rh(III)-catalyzed oxidative olefination of vinylic C-H bonds: efficient and selective access to di-unsaturated α-amino acid derivatives and other linear 1,3-butadienes. , 2011, Chemistry.

[9]  J. Muzart,et al.  Intermolecular dehydrogenative Heck reactions. , 2011, Chemical reviews.

[10]  C. Yeung,et al.  Catalytic dehydrogenative cross-coupling: forming carbon-carbon bonds by oxidizing two carbon-hydrogen bonds. , 2011, Chemical reviews.

[11]  T. Satoh,et al.  Transition-Metal-CatalyzedRegioselective Arylation and Vinylation of CarboxylicAcids , 2010 .

[12]  Chenglin Sun,et al.  Palladium-catalyzed cross-coupling of internal alkenes with terminal alkenes to functionalized 1,3-butadienes using C-H bond activation: efficient synthesis of bicyclic pyridones. , 2010, Angewandte Chemie.

[13]  T. Loh,et al.  Palladium-catalyzed direct cross-coupling reaction between indenes and electron-deficient alkenes , 2010 .

[14]  S. Tian,et al.  A highly tunable stereoselective olefination of semistabilized triphenylphosphonium ylides with N-sulfonyl imines. , 2010, Journal of the American Chemical Society.

[15]  Melanie S Sanford,et al.  Palladium-catalyzed ligand-directed C-H functionalization reactions. , 2010, Chemical reviews.

[16]  T. Loh,et al.  Direct cross-coupling reaction of simple alkenes with acrylates catalyzed by palladium catalyst. , 2009, Journal of the American Chemical Society.

[17]  J. Bergueiro,et al.  Hiyama cross-coupling reaction in the stereospecific synthesis of retinoids. , 2009, Organic letters.

[18]  B. Trost,et al.  An atom-economic and selective ruthenium-catalyzed redox isomerization of propargylic alcohols. An efficient strategy for the synthesis of leukotrienes. , 2008, Journal of the American Chemical Society.

[19]  G. Georg,et al.  Palladium(II)-catalyzed direct arylation of enaminones using organotrifluoroborates. , 2008, Journal of the American Chemical Society.

[20]  J. Ellman,et al.  The stereoselective formation of bicyclic enamines with bridgehead unsaturation via tandem C-H bond activation/alkenylation/electrocyclization. , 2008, Journal of the American Chemical Society.

[21]  T. Nishimura,et al.  Ruthenium/Halide Catalytic System for CC Bond Forming Reaction between Alkynes and Unsaturated Carbonyl Compounds , 2007 .

[22]  J. Montenegro,et al.  Highly convergent, stereospecific synthesis of 11-cis-retinoids by metal-catalyzed cross-coupling reactions of (Z)-1-alkenylmetals. , 2007, The Journal of organic chemistry.

[23]  M. Martinelli,et al.  C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents. , 2007, Chemical reviews.

[24]  J. V. Nelson,et al.  Stereoselective Aldol Condensations , 2007 .

[25]  E. Negishi.  Transition Metal-Catalyzed Organometallic Reactions that Have Revolutionized Organic Synthesis , 2007 .

[26]  S. Sakaguchi,et al.  Oxidative cross-coupling of acrylates with vinyl carboxylates catalyzed by a Pd(OAc)2/HPMoV/O2 system. , 2004, Organic letters.

[27]  R. Alves,et al.  Palladium catalyzed transformations of monoterpenes: stereoselective deuteriation and oxidative dimerization of camphene , 2004 .

[28]  E. V. Gusevskaya,et al.  Palladium-catalyzed oxidation of monoterpenes: novel tandem oxidative coupling–oxidation of camphene by dioxygen , 2001 .

[29]  T. Kitamura,et al.  Catalytic functionalization of arenes and alkanes via C-H bond activation. , 2001, Accounts of chemical research.

[30]  S. Tanumihardjo.  Synthesis of 10,11,14,15‐13C4‐and 14,15‐13C2‐retinyl acetate , 2001 .

[31]  Torrado,et al.  A pericyclic cascade to the stereocontrolled synthesis of 9-cis-retinoids , 2000, The Journal of organic chemistry.

[32]  K. Nakanishi,et al.  Efficient Synthesis of 11-cis-Retinoids , 1999 .

[33]  Norio Miyaura,et al.  Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds , 1995 .

[34]  Ken‐Tsung Wong,et al.  Silyl-substituted conjugated dienes : versatile building blocks in organic synthesis , 1993 .

[35]  A. Reitz,et al.  The Wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions. Stereochemistry, mechanism, and selected synthetic aspects , 1989 .

[36]  John K. Stille,et al.  The Palladium‐Catalyzed Cross‐Coupling Reactions of Organotin Reagents with Organic Electrophiles [New Synthetic Methods (58)] , 1986 .

[37]  C. Neukom,et al.  Total synthesis of (5S,6R,7E,9E,11Z,14Z)-5-hydroxy-6-[(2R)-2-amino-2-(carboxyethyl)thio]-7,9,11,14-eicosatetraenoic acid, a potent SRS-A , 1980 .

[38]  J. Gruber,et al.  Epoxidation of retinol and the structure of “chromogen 574” , 1980 .

[39]  W. Rojahn,et al.  Die synthese von dihydro-iso-santalol und verwandten verbindungen , 1978 .

[40]  M. Tishler,et al.  SYNTHESIS OF VITAMIN A , 1949 .