One-pot Suzuki–Heck relay to prepare industrially valuable intermediates using the Pd–Cy*Phine catalyst system

A rare example of a one-pot, palladium-catalyzed Suzuki–Heck sequence has been developed with applicability to APIs and organoelectronic materials. High throughput screening was used to expedite development and survey strategies. Interchangeability of the coupling partners and the avoidance of intermediate isolation gives operational flexibility, which can be used to improve process efficiency and suppress by-product formation.

[1]  Xingshu Li,et al.  New multi-target-directed small molecules against Alzheimer's disease: a combination of resveratrol and clioquinol. , 2014, Organic & biomolecular chemistry.

[2]  Yong Yang,et al.  Palladium precatalysts containing meta-terarylphosphine ligands for expedient copper-free Sonogashira cross-coupling reactions , 2015 .

[3]  C. Nájera,et al.  Palladium-catalyzed cross-coupling reactions of potassium alkenyltrifluoroborates with organic halides in aqueous media. , 2009, The Journal of organic chemistry.

[4]  L. Djakovitch,et al.  One‐Pot Suzuki/Heck Sequence for the Synthesis of (E)‐Stilbenes Featuring a Recyclable Silica‐Supported Palladium Catalyst via a Multi‐Component Reaction in 1,3‐Propanediol , 2010 .

[5]  Arno Kraft,et al.  Electroluminescent Conjugated Polymers-Seeing Polymers in a New Light. , 1998, Angewandte Chemie.

[6]  E. Åkerblom,et al.  Vinylated linear P2 pyrimidinyloxyphenylglycine based inhibitors of the HCV NS3/4A protease and corresponding macrocycles. , 2014, Bioorganic & medicinal chemistry.

[7]  D. O’Shea,et al.  Generation of substituted styrenes via Suzuki cross-coupling of aryl halides with 2,4,6-trivinylcyclotriboroxane. , 2002, The Journal of organic chemistry.

[8]  M. Fakis,et al.  Quadrupolar benzobisthiazole-cored arylamines as highly efficient two-photon absorbing fluorophores. , 2014, Organic letters.

[9]  S. Pandey,et al.  One‐Pot Palladium‐Catalyzed Cross‐Coupling Treble of Borylation, the Suzuki Reaction and Amination , 2017 .

[10]  R. Heck Palladium‐Catalyzed Vinylation of Organic Halides , 2005 .

[11]  R. Pettit,et al.  Antineoplastic agents. 445. Synthesis and evaluation of structural modifications of (Z)- and (E)-combretastatin A-41. , 2005, Journal of medicinal chemistry.

[12]  R. Heck,et al.  Palladium-catalyzed vinylic hydrogen substitution reactions with aryl, benzyl, and styryl halides , 1972 .

[13]  M. Inoue,et al.  Facile synthesis of 1,7,8-trifluoro-2-naphthol via DMAP catalyzed cycloaromatization , 2014 .

[14]  Daohang He,et al.  Synthesis, biological evaluation, and structure-activity relationship study of novel stilbene derivatives as potential fungicidal agents. , 2015, Journal of agricultural and food chemistry.

[15]  Yuichiro Watanabe,et al.  Discovery of a 2-hydroxyacetophenone derivative as an outstanding linker to enhance potency and β-selectivity of liver X receptor agonist. , 2016, Bioorganic & medicinal chemistry.

[16]  I. Beletskaya,et al.  The heck reaction as a sharpening stone of palladium catalysis. , 2000, Chemical reviews.

[17]  E. Lephart,et al.  A new synthesis of 4'-resveratrol esters and evaluation of the potential for anti-depressant activity. , 2013, Bioorganic & medicinal chemistry letters.

[18]  Wenqin Wu,et al.  Palladium-meta-terarylphosphine catalyst for the Mizoroki-Heck reaction of (hetero)aryl bromides and functional olefins. , 2015, The Journal of organic chemistry.

[19]  G. G. Stokes "J." , 1890, The New Yale Book of Quotations.

[20]  Gary T. Wang,et al.  Lead optimization of methionine aminopeptidase-2 (MetAP2) inhibitors containing sulfonamides of 5,6-disubstituted anthranilic acids. , 2007, Bioorganic & medicinal chemistry letters.