Literature DB >> 21510631

Palladium-catalyzed hydrofunctionalization of vinyl phenol derivatives with heteroaromatics.

Tejas P Pathak1, Matthew S Sigman.   

Abstract

A hydroheteroarylation reaction of vinyl phenols using an alkyl chloride as the sacrificial hydride source is reported. The method tolerates a wide range of heterocycles as the exogenous nucleophile including indoles and pyrroles. The resulting products are easily processed to biologically relevant scaffolds.

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Year:  2011        PMID： 21510631      PMCID： PMC3324091          DOI： 10.1021/ol200913r

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  22 in total

1.  Nickel-catalyzed hydroheteroarylation of vinylarenes.

Authors:  Yoshiaki Nakao; Natsuko Kashihara; Kyalo Stephen Kanyiva; Tamejiro Hiyama
Journal:  Angew Chem Int Ed Engl       Date:  2010-06-14       Impact factor: 15.336

2.  Synthesis and preliminary biological studies of 3-substituted indoles accessed by a palladium-catalyzed enantioselective alkene difunctionalization reaction.

Authors:  Tejas P Pathak; Keith M Gligorich; Bryan E Welm; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2010-06-16       Impact factor: 15.419

3.  Palladium(II)-catalyzed aerobic hydroalkoxylation of styrenes containing a phenol.

Authors:  Keith M Gligorich; Mitchell J Schultz; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2006-03-08       Impact factor: 15.419

4.  Room-temperature alkyl-alkyl Suzuki cross-coupling of alkyl bromides that possess beta hydrogens.

Authors:  M R Netherton; C Dai; K Neuschütz; G C Fu
Journal:  J Am Chem Soc       Date:  2001-10-17       Impact factor: 15.419

5.  New ortho-quinone methide formation: application to three-component coupling of isocyanides, aldehydes and phenols.

Authors:  Laurent El Kaïm; Laurence Grimaud; Julie Oble
Journal:  Org Biomol Chem       Date:  2006-08-08       Impact factor: 3.876

6.  Palladium-catalyzed hydroarylation of 1,3-dienes with boronic esters via reductive formation of pi-allyl palladium intermediates under oxidative conditions.

Authors:  Longyan Liao; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2010-08-04       Impact factor: 15.419

7.  Optimization of small molecule agonists of the thrombopoietin (Tpo) receptor derived from a benzo[a]carbazole hit scaffold.

Authors:  Thomas H Marsilje; Phil B Alper; Wenshuo Lu; Daniel Mutnick; Pierre-Yves Michellys; Yun He; Donald S Karanewsky; Donald Chow; Andrea Gerken; Jianmin Lao; Min-Ju Kim; H Martin Seidel; Shin-Shay Tian
Journal:  Bioorg Med Chem Lett       Date:  2008-08-26       Impact factor: 2.823

8.  Palladium-catalyzed hydroalkylation of styrenes with organozinc reagents to form carbon-carbon sp3-sp3 bonds under oxidative conditions.

Authors:  Kaveri Balan Urkalan; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2009-12-23       Impact factor: 15.419

9.  Elucidating reactivity differences in palladium-catalyzed coupling processes: the chemistry of palladium hydrides.

Authors:  Ivory D Hills; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2004-10-20       Impact factor: 15.419

Review 10.  Synthetic applications of palladium-catalyzed hydroarylation and related systems.

Authors:  David Mitchell; Hannah Yu
Journal:  Curr Opin Drug Discov Devel       Date:  2003-11
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  9 in total

1.  Palladium(II)-catalyzed enantio- and diastereoselective synthesis of pyrrolidine derivatives.

Authors:  Ranjan Jana; Tejas P Pathak; Katrina H Jensen; Matthew S Sigman
Journal:  Org Lett       Date:  2012-08-08       Impact factor: 6.005

2.  Multicomponent Condensation Reactions via ortho-Quinone Methides.

Authors:  Emily E Allen; Calvin Zhu; James S Panek; Scott E Schaus
Journal:  Org Lett       Date:  2017-03-30       Impact factor: 6.005

3.  Applications of ortho-quinone methide intermediates in catalysis and asymmetric synthesis.

Authors:  Tejas P Pathak; Matthew S Sigman
Journal:  J Org Chem       Date:  2011-10-19       Impact factor: 4.354

4.  Palladium-catalyzed 1,4-difunctionalization of butadiene to form skipped polyenes.

Authors:  Matthew S McCammant; Longyan Liao; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2013-03-12       Impact factor: 15.419

5.  Enantioselective addition of boronates to o-quinone methides catalyzed by chiral biphenols.

Authors:  Yi Luan; Scott E Schaus
Journal:  J Am Chem Soc       Date:  2012-12-03       Impact factor: 15.419

6.  Copper-catalyzed recycling of halogen activating groups via 1,3-halogen migration.

Authors:  R David Grigg; Ryan Van Hoveln; Jennifer M Schomaker
Journal:  J Am Chem Soc       Date:  2012-09-19       Impact factor: 15.419

7.  Redox-neutral α,β-difunctionalization of cyclic amines.

Authors:  Weijie Chen; YoungKu Kang; Richard G Wilde; Daniel Seidel
Journal:  Angew Chem Int Ed Engl       Date:  2014-04-01       Impact factor: 15.336

8.  Exploring the Catalytic Promiscuity of Phenolic Acid Decarboxylases: Asymmetric, 1,6-Conjugate Addition of Nucleophiles Across 4-Hydroxystyrene.

Authors:  Stefan E Payer; Xiang Sheng; Hannah Pollak; Christiane Wuensch; Georg Steinkellner; Fahmi Himo; Silvia M Glueck; Kurt Faber
Journal:  Adv Synth Catal       Date:  2017-05-08       Impact factor: 5.837

9.  A Modular Synthesis of Teraryl-Based α-Helix Mimetics, Part 3: Iodophenyltriflate Core Fragments Featuring Side Chains of Proteinogenic Amino Acids.

Authors:  Melanie Trobe; Martin Vareka; Till Schreiner; Patrick Dobrounig; Carina Doler; Ella B Holzinger; Andreas Steinegger; Rolf Breinbauer
Journal:  European J Org Chem       Date:  2022-02-24
  9 in total

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