Literature DB >> 24047468

Pd(0)-catalyzed 1,1-diarylation of ethylene and allylic carbonates.

Vaneet Saini1, Longyan Liao, Qiaofeng Wang, Ranjan Jana, Matthew S Sigman.   

Abstract

An efficient protocol for the one-step synthesis of biologically relevant 1,1-diarylalkanes has been described. This reaction introduces two different aryl groups across the terminal end of simple feedstock alkenes such as ethylene and allylic carbonates. The propensity to generate π-benzylpalladium intermediates dictates the exclusive 1,1-regioselectivity observed in the product.

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Year:  2013        PMID： 24047468      PMCID： PMC3955058          DOI： 10.1021/ol4023358

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


  32 in total

1.  Vaccinia virus virulence factor N1L is a novel promising target for antiviral therapeutic intervention.

Authors:  Anton V Cheltsov; Mika Aoyagi; Alexander Aleshin; Eric Chi-Wang Yu; Taylor Gilliland; Dayong Zhai; Andrey A Bobkov; John C Reed; Robert C Liddington; Ruben Abagyan
Journal:  J Med Chem       Date:  2010-05-27       Impact factor: 7.446

2.  Enantioselective preparation of 1,1-diarylethanes: aldehydes as removable steering groups for asymmetric synthesis.

Authors:  Thomas C Fessard; Stephen P Andrews; Hajime Motoyoshi; Erick M Carreira
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

3.  A palladium-catalyzed three-component cross-coupling of conjugated dienes or terminal alkenes with vinyl triflates and boronic acids.

Authors:  Longyan Liao; Ranjan Jana; Kaveri Balan Urkalan; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2011-03-30       Impact factor: 15.419

4.  Metal-free carbon-carbon bond-forming reductive coupling between boronic acids and tosylhydrazones.

Authors:  José Barluenga; María Tomás-Gamasa; Fernando Aznar; Carlos Valdés
Journal:  Nat Chem       Date:  2009-08-16       Impact factor: 24.427

5.  Highly enantioselective hydrogenation of styrenes directed by 2'-hydroxyl groups.

Authors:  Xiang Wang; Anil Guram; Seb Caille; Jack Hu; J P Preston; Michael Ronk; Shawn Walker
Journal:  Org Lett       Date:  2011-03-08       Impact factor: 6.005

6.  Palladium-catalyzed 1,1-difunctionalization of ethylene.

Authors:  Vaneet Saini; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2012-07-10       Impact factor: 15.419

7.  Distinctive meta-directing group effect for iridium-catalyzed 1,1-diarylalkene enantioselective hydrogenation.

Authors:  Elizabeth N Bess; Matthew S Sigman
Journal:  Org Lett       Date:  2013-01-11       Impact factor: 6.005

8.  Functional-group-tolerant, nickel-catalyzed cross-coupling reaction for enantioselective construction of tertiary methyl-bearing stereocenters.

Authors:  Hanna M Wisniewska; Elizabeth C Swift; Elizabeth R Jarvo
Journal:  J Am Chem Soc       Date:  2013-06-10       Impact factor: 15.419

9.  Traceless directing group for stereospecific nickel-catalyzed alkyl-alkyl cross-coupling reactions.

Authors:  Margaret A Greene; Ivelina M Yonova; Florence J Williams; Elizabeth R Jarvo
Journal:  Org Lett       Date:  2012-05-08       Impact factor: 6.005

10.  Development of a screen to identify selective small molecules active against patient-derived metastatic and chemoresistant breast cancer cells.

Authors:  Keith M Gligorich; Rachel M Vaden; Dawne N Shelton; Guoying Wang; Cindy B Matsen; Ryan E Looper; Matthew S Sigman; Bryan E Welm
Journal:  Breast Cancer Res       Date:  2013       Impact factor: 6.466
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  16 in total

1.  Enantioselective 1,1-arylborylation of alkenes: merging chiral anion phase transfer with Pd catalysis.

Authors:  Hosea M Nelson; Brett D Williams; Javier Miró; F Dean Toste
Journal:  J Am Chem Soc       Date:  2015-02-27       Impact factor: 15.419

2.  Mechanistic Investigations of the Pd(0)-Catalyzed Enantioselective 1,1-Diarylation of Benzyl Acrylates.

Authors:  Manuel Orlandi; Margaret J Hilton; Eiji Yamamoto; F Dean Toste; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2017-08-30       Impact factor: 15.419

3.  Catalyst-Controlled 1,2- and 1,1-Arylboration of α-Alkyl Alkenyl Arenes.

Authors:  Allison M Bergmann; Stanna K Dorn; Kevin B Smith; Kaitlyn M Logan; M Kevin Brown
Journal:  Angew Chem Int Ed Engl       Date:  2019-01-09       Impact factor: 15.336

4.  Ni-Catalyzed Arylbenzylation of Alkenylarenes: Kinetic Studies Reveal Autocatalysis by ZnX2 *.

Authors:  Roshan K Dhungana; Rishi R Sapkota; Laura M Wickham; Doleshwar Niroula; Bijay Shrestha; Ramesh Giri
Journal:  Angew Chem Int Ed Engl       Date:  2021-09-15       Impact factor: 16.823

5.  Development and Analysis of a Pd(0)-Catalyzed Enantioselective 1,1-Diarylation of Acrylates Enabled by Chiral Anion Phase Transfer.

Authors:  Eiji Yamamoto; Margaret J Hilton; Manuel Orlandi; Vaneet Saini; F Dean Toste; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2016-11-30       Impact factor: 15.419

6.  Stereospecific nickel-catalyzed cross-coupling reactions of alkyl Grignard reagents and identification of selective anti-breast-cancer agents.

Authors:  Ivelina M Yonova; A George Johnson; Charlotte A Osborne; Curtis E Moore; Naomi S Morrissette; Elizabeth R Jarvo
Journal:  Angew Chem Int Ed Engl       Date:  2014-01-29       Impact factor: 15.336

7.  Pd(Quinox)-Catalyzed Allylic Relay Suzuki Reactions of Secondary Homostyrenyl Tosylates via Alkene-Assisted Oxidative Addition.

Authors:  Benjamin J Stokes; Amanda J Bischoff; Matthew S Sigman
Journal:  Chem Sci       Date:  2014-06-01       Impact factor: 9.825

8.  Ni(I)-Catalyzed β,δ-Vinylarylation of γ,δ-Alkenyl α-Cyanocarboxylic Esters via Contraction of Transient Nickellacycles.

Authors:  Roshan K Dhungana; Shekhar Kc; Prakash Basnet; Vivek Aryal; Lucas J Chesley; Ramesh Giri
Journal:  ACS Catal       Date:  2019-10-29       Impact factor: 13.700

9.  Palladium-catalyzed enantioselective 1,1-fluoroarylation of aminoalkenes.

Authors:  Ying He; Zhenyu Yang; Richard T Thornbury; F Dean Toste
Journal:  J Am Chem Soc       Date:  2015-09-17       Impact factor: 15.419

Review 10.  Walking metals: catalytic difunctionalization of alkenes at nonclassical sites.

Authors:  Roshan K Dhungana; Rishi R Sapkota; Doleshwar Niroula; Ramesh Giri
Journal:  Chem Sci       Date:  2020-09-07       Impact factor: 9.825
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