Enantioselective palladium-catalyzed diarylation of unactivated alkenes.

Enantioselective Pd-catalyzed diarylation of unactivated alkenes between arenediazonium salts and arylboronic acids has been developed. This method provides an efficient route to dihydrobenzofurans with all-carbon quaternary centers in good yields with 88-99% ee. This reaction proceeding under mild and open-flask conditions is compatible with a variety of functional groups, including cyano, ketone, ester, amide, bromine and free hydroxyl groups.

[1]  Junliang Zhang,et al.  Enantioselective Dicarbofunctionalization of Unactivated Alkenes by Pd-Catalyzed Tandem Heck/Suzuki-Coupling Reaction. , 2019, Angewandte Chemie.

[2]  Junliang Zhang,et al.  Palladium/XuPhos-Catalyzed Enantioselective Carboiodination of Olefin-Tethered Aryl Iodides. , 2019, Journal of the American Chemical Society.

[3]  Yanxing Jia,et al.  Synthetic approaches to natural products containing 2,3-dihydrobenzofuran skeleton. , 2019, Natural product reports.

[4]  M. Lautens,et al.  Pd-catalyzed dearomative arylborylation of indoles , 2019, Chemical Science.

[5]  R. B. Sunoj,et al.  Harnessing Noncovalent Interactions in Dual-Catalytic Enantioselective Heck-Matsuda Arylation. , 2019, Journal of the American Chemical Society.

[6]  Yu Ping,et al.  Construction of Quaternary Stereocenters by Palladium-Catalyzed Carbopalladation-Initiated Cascade Reactions. , 2018, Angewandte Chemie.

[7]  E. V. Van der Eycken,et al.  Recent Advances in Phthalan and Coumaran Chemistry , 2018, ChemistryOpen.

[8]  Wangqing Kong,et al.  Ni-Catalyzed Enantioselective Reductive Diarylation of Activated Alkenes by Domino Cyclization/Cross-Coupling. , 2018, Journal of the American Chemical Society.

[9]  C. R. Correia,et al.  Chiral N,N Ligands Enabling Palladium-Catalyzed Enantioselective Intramolecular Heck-Matsuda Carbonylation Reactions by Sequential Migratory and CO Insertions. , 2018, Angewandte Chemie.

[10]  R. Giri,et al.  Transition Metal-Catalyzed Dicarbofunctionalization of Unactivated Olefins. , 2018, Chemical record.

[11]  M. K. Brown,et al.  Nickel-Catalyzed Stereoselective Diarylation of Alkenylarenes. , 2018, Journal of the American Chemical Society.

[12]  Junliang Zhang,et al.  Palladium-Catalyzed Enantioselective Reductive Heck Reactions: Convenient Access to 3,3-Disubstituted 2,3-Dihydrobenzofuran. , 2018, Angewandte Chemie.

[13]  C. R. Correia,et al.  Enantioselective, Noncovalent, Substrate-Directable Heck-Matsuda and Oxidative Heck Arylations of Unactivated Five-Membered Carbocyclic Olefins. , 2018, Chemistry.

[14]  R. Giri,et al.  Strategies toward Dicarbofunctionalization of Unactivated Olefins by Combined Heck Carbometalation and Cross-Coupling. , 2018, The Journal of organic chemistry.

[15]  Yu Ping,et al.  Nickel-Catalyzed Domino Heck Cyclization/Suzuki Coupling for the Synthesis of 3,3-Disubstituted Oxindoles. , 2018, Organic letters.

[16]  C. R. Correia,et al.  Enantioselective Oxy-Heck-Matsuda Arylations: Expeditious Synthesis of Dihydrobenzofuran Systems and Total Synthesis of the Neolignan (-)-Conocarpan , 2018 .

[17]  R. Giri,et al.  Ni-catalysed regioselective 1,2-diarylation of unactivated olefins by stabilizing Heck intermediates as pyridylsilyl-coordinated transient metallacycles , 2017, Chemical science.

[18]  Wanfang Li,et al.  Nickel-catalyzed difunctionalization of allyl moieties using organoboronic acids and halides with divergent regioselectivities , 2017, Chemical science.

[19]  Eiji Yamamoto,et al.  Mechanistic Investigations of the Pd(0)-Catalyzed Enantioselective 1,1-Diarylation of Benzyl Acrylates. , 2017, Journal of the American Chemical Society.

[20]  V. Tran,et al.  Nickel-Catalyzed β,γ-Dicarbofunctionalization of Alkenyl Carbonyl Compounds via Conjunctive Cross-Coupling. , 2017, Journal of the American Chemical Society.

[21]  R. Giri,et al.  Ni-Catalyzed Regioselective 1,2-Dicarbofunctionalization of Olefins by Intercepting Heck Intermediates as Imine-Stabilized Transient Metallacycles. , 2017, Journal of the American Chemical Society.

[22]  S. Staben,et al.  A General Strategy for the Construction of Functionalized Azaindolines via Domino Palladium-Catalyzed Heck Cyclization/Suzuki Coupling. , 2017, Organic letters.

[23]  Yi‐Xia Jia,et al.  Enantioselective Dearomative Difunctionalization of Indoles by Palladium-Catalyzed Heck/Sonogashira Sequence. , 2017, Angewandte Chemie.

[24]  R. B. Sunoj,et al.  Enantioselective Heck-Matsuda Arylations through Chiral Anion Phase-Transfer of Aryl Diazonium Salts. , 2017, Angewandte Chemie.

[25]  Jieping Zhu,et al.  Water as a Hydride Source in Palladium-Catalyzed Enantioselective Reductive Heck Reactions. , 2017, Angewandte Chemie.

[26]  Fei Wang,et al.  Asymmetric Cu-Catalyzed Intermolecular Trifluoromethylarylation of Styrenes: Enantioselective Arylation of Benzylic Radicals. , 2017, Journal of the American Chemical Society.

[27]  C. R. Correia,et al.  Non-Covalent Carbonyl-Directed Heck–Matsuda Desymmetrizations: Synthesis of Cyclopentene-Fused Spirooxindoles, Spirolactones, and Spirolactams , 2017 .

[28]  F. Toste,et al.  Development and Analysis of a Pd(0)-Catalyzed Enantioselective 1,1-Diarylation of Acrylates Enabled by Chiral Anion Phase Transfer. , 2016, Journal of the American Chemical Society.

[29]  Fei Wang,et al.  Enantioselective Copper-Catalyzed Intermolecular Cyanotrifluoromethylation of Alkenes via Radical Process. , 2016, Journal of the American Chemical Society.

[30]  Teng Xu,et al.  Palladium-catalyzed dearomative arylalkynylation of indoles. , 2016, Chemical communications.

[31]  K. Engle,et al.  β,γ-Vicinal Dicarbofunctionalization of Alkenyl Carbonyl Compounds via Directed Nucleopalladation. , 2016, Journal of the American Chemical Society.

[32]  C. R. Correia,et al.  Enantioselective total synthesis of the highly selective sphingosine-1-receptor VPC01091 by the Heck desymmetrization of a non-activated cyclopentene-fused spiro-pyrrolidinone. , 2016, Organic & biomolecular chemistry.

[33]  C. R. Correia,et al.  Noncovalent Substrate-Directed Enantioselective Heck Reactions: Synthesis of S- and P-Stereogenic Heterocycles. , 2016, Chemistry.

[34]  David A Petrone,et al.  Pd(0)-Catalyzed Dearomative Diarylation of Indoles. , 2016, Chemistry.

[35]  Jieping Zhu,et al.  Palladium-Catalyzed Enantioselective Domino Heck/Intermolecular C-H Bond Functionalization: Development and Application to the Synthesis of (+)-Esermethole. , 2015, Journal of the American Chemical Society.

[36]  C. R. Correia,et al.  Quaternary Stereogenic Centers through Enantioselective Heck Arylation of Acyclic Olefins with Aryldiazonium Salts: Application in a Concise Synthesis of (R)-Verapamil. , 2015, Angewandte Chemie.

[37]  M. K. Brown,et al.  Catalytic Enantioselective Diarylation of Alkenes. , 2015, Journal of the American Chemical Society.

[38]  E. V. Van der Eycken,et al.  Domino Heck/borylation sequence towards indolinone-3-methyl boronic esters: trapping of the σ-alkylpalladium intermediate with boron. , 2015, Chemical communications.

[39]  G. Yue,et al.  Palladium-catalyzed asymmetric reductive heck reaction of aryl halides. , 2015, Angewandte Chemie.

[40]  Teng Xu,et al.  Enantioselective Arylative Dearomatization of Indoles via Pd-Catalyzed Intramolecular Reductive Heck Reactions. , 2015, Journal of the American Chemical Society.

[41]  Brett D. Williams,et al.  Enantioselective 1,1-arylborylation of alkenes: merging chiral anion phase transfer with Pd catalysis. , 2015, Journal of the American Chemical Society.

[42]  David A Petrone,et al.  Diastereoselective palladium-catalyzed arylcyanation/heteroarylcyanation of enantioenriched N-allylcarboxamides. , 2014, Organic letters.

[43]  M. K. Brown,et al.  Diarylation of alkenes by a Cu-catalyzed migratory insertion/cross-coupling cascade. , 2014, Journal of the American Chemical Society.

[44]  C. R. Correia,et al.  Stereoselective synthesis of aryl cyclopentene scaffolds by Heck-Matsuda desymmetrization of 3-cyclopentenol. , 2014, Chemistry.

[45]  B. Stokes,et al.  A Palladium-Catalyzed Three-Component-Coupling Strategy for the Differential Vicinal Diarylation of Terminal 1,3-Dienes , 2014, Organic letters.

[46]  B. Stokes,et al.  The strategic generation and interception of palladium-hydrides for use in alkene functionalization reactions , 2014 .

[47]  G. C. Fu,et al.  Catalytic Enantioselective Cyclization/Cross-Coupling with Alkyl Electrophiles , 2014, Journal of the American Chemical Society.

[48]  Ren‐Jie Song,et al.  Alkylation of terminal alkynes with transient σ-alkylpalladium(II) complexes: a carboalkynylation route to alkyl-substituted alkynes. , 2014, Chemistry.

[49]  O. Wiest,et al.  Mechanism, Reactivity, and Selectivity in Palladium-Catalyzed Redox-Relay Heck Arylations of Alkenyl Alcohols , 2014, Journal of the American Chemical Society.

[50]  C. R. Correia,et al.  Intermolecular enantioselective Heck-Matsuda arylations of acyclic olefins: application to the synthesis of β-aryl-γ-lactones and β-aryl aldehydes. , 2013, The Journal of organic chemistry.

[51]  T. Mei,et al.  Enantioselective Heck Arylations of Acyclic Alkenyl Alcohols Using a Redox-Relay Strategy , 2012, Science.

[52]  B. Seashore-Ludlow,et al.  Domino carbopalladation-cross-coupling for the synthesis of 3,3-disubstituted oxindoles. , 2012, Organic letters.

[53]  C. R. Correia,et al.  The first examples of the enantioselective Heck–Matsuda reaction: arylation of unactivated cyclic olefins using chiral bisoxazolines , 2012 .

[54]  M. Naguib,et al.  A synthetic approach for (S)-(3-benzyl-3-methyl-2,3-dihydro-benzofuran-6-yl)-piperidin-1-yl-methanone, a selective CB2 receptor agonist , 2012 .

[55]  José Duca,et al.  Synthesis of new 4,5-dihydrofuranoindoles and their evaluation as HCV NS5B polymerase inhibitors. , 2012, Organic letters.

[56]  T. Sheppard Strategies for the Synthesis of 2,3-Dihydrobenzofurans , 2011 .

[57]  M. Lautens,et al.  Palladium-catalyzed carboiodination of alkenes: carbon-carbon bond formation with retention of reactive functionality. , 2011, Journal of the American Chemical Society.

[58]  L. Neuville,et al.  Palladium-catalyzed carbo-heterofunctionalization of alkenes for the synthesis of oxindoles and spirooxindoles. , 2010, Organic letters.

[59]  Claudio N. Cavasotto,et al.  2,3‐Dihydro‐1‐Benzofuran Derivatives as a Series of Potent Selective Cannabinoid Receptor 2 Agonists: Design, Synthesis, and Binding Mode Prediction through Ligand‐Steered Modeling , 2009, ChemMedChem.

[60]  M. Pineschi,et al.  Recent Progress in the Synthesis of 2,3-Dihydrobenzofurans , 2009 .

[61]  M. Moreno-Mañas,et al.  Diazonium salts as substrates in palladium-catalyzed cross-coupling reactions. , 2006, Chemical Reviews.

[62]  K. Nicolaou,et al.  Studies toward diazonamide A: development of a hetero-pinacol macrocyclization cascade for the construction of the bis-macrocyclic framework of the originally proposed structure. , 2004, Journal of the American Chemical Society.

[63]  K. Nicolaou,et al.  Construction of the complete aromatic core of diazonamide A by a novel hetero pinacol macrocyclization cascade reaction , 2001 .

[64]  P. Diaz,et al.  NEW SYNTHETIC RETINOIDS OBTAINED BY PALLADIUM-CATALYZED TANDEM CYCLISATION-HYDRIDE CAPTURE PROCESS , 1998 .

[65]  D. Phillips Palladium‐Catalyzed Heterocyclization: A Carbon‐Centered Approach , 2017 .

[66]  Hongbin Zhang,et al.  Research Progress on the Synthesis of Morphine Alkaloids , 2017 .

[67]  V. Sridharan,et al.  Bimetallic (Cu/Pd) catalytic cascade reactions to 3,3-disubstituted oxindole analogues , 2014 .

[68]  T. Hudlický,et al.  Synthesis of morphine alkaloids and derivatives. , 2012, Topics in current chemistry.

[69]  N. Chida Recent advances in the synthesis of morphine and related alkaloids. , 2011, Topics in current chemistry.