Literature DB >> 21449562

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

Longyan Liao1, Ranjan Jana, Kaveri Balan Urkalan, Matthew S Sigman.   

Abstract

A three-component coupling of vinyl triflates and boronic acids to alkenes catalyzed by palladium is reported. Using 1,3-dienes, selective 1,2-alkene difunction-alization is observed, whereas the use of terminal alkenes results in 1,1-alkene difunctionalization. The reaction outcome is attributed to the formation of stabilized, cationic Pd-π-allyl intermediates to regulate β-hydride elimination.

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Year:  2011        PMID： 21449562      PMCID： PMC3084658          DOI： 10.1021/ja201358b

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  42 in total

1.  Highly regioselective Pd-catalyzed intermolecular aminoacetoxylation of alkenes and evidence for cis-aminopalladation and S(N)2 C-O bond formation.

Authors:  Guosheng Liu; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2006-06-07       Impact factor: 15.419

2.  Palladium-catalyzed intermolecular aminofluorination of styrenes.

Authors:  Shuifa Qiu; Tao Xu; Juan Zhou; Yinlong Guo; Guosheng Liu
Journal:  J Am Chem Soc       Date:  2010-03-10       Impact factor: 15.419

3.  Pd-catalyzed three-component coupling of N-tosylhydrazone, terminal alkyne, and aryl halide.

Authors:  Lei Zhou; Fei Ye; Yan Zhang; Jianbo Wang
Journal:  J Am Chem Soc       Date:  2010-10-06       Impact factor: 15.419

4.  Decarboxylative benzylations of alkynes and ketones.

Authors:  Robert R P Torregrosa; Yamuna Ariyarathna; Kalicharan Chattopadhyay; Jon A Tunge
Journal:  J Am Chem Soc       Date:  2010-07-14       Impact factor: 15.419

5.  Highly efficient route to o-Allylbiaryls via palladium-catalyzed three-component coupling of benzynes, allylic halides, and aryl organometallic reagents.

Authors:  Thiruvellore Thatai Jayanth; Masilamani Jeganmohan; Chien-Hong Cheng
Journal:  Org Lett       Date:  2005-07-07       Impact factor: 6.005

6.  Palladium-catalyzed diacetoxylation of alkenes with molecular oxygen as sole oxidant.

Authors:  Azhong Wang; Huanfeng Jiang; Huoji Chen
Journal:  J Am Chem Soc       Date:  2009-03-25       Impact factor: 15.419

7.  Palladium-catalyzed insertion of alpha-diazoesters into vinyl halides to generate alpha,beta-unsaturated gamma-amino esters.

Authors:  Romas Kudirka; Sean K J Devine; Christopher S Adams; David L Van Vranken
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

8.  Catalytic asymmetric allylic and homoallylic diamination of terminal olefins via formal C-H activation.

Authors:  Haifeng Du; Baoguo Zhao; Yian Shi
Journal:  J Am Chem Soc       Date:  2008-06-13       Impact factor: 15.419

Review 9.  C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents.

Authors:  Egle M Beccalli; Gianluigi Broggini; Michela Martinelli; Silvia Sottocornola
Journal:  Chem Rev       Date:  2007-11-01       Impact factor: 60.622

Review 10.  Recent advances in noble metal nanocatalysts for Suzuki and Heck cross-coupling reactions.

Authors:  Radha Narayanan
Journal:  Molecules       Date:  2010-03-25       Impact factor: 4.411
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  43 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.  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

3.  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

4.  Mechanism and Selectivity in the Pd-Catalyzed Difunctionalization of Isoprene.

Authors:  Liping Xu; Xin Zhang; Matthew S McCammant; Matthew S Sigman; Yun-Dong Wu; Olaf Wiest
Journal:  J Org Chem       Date:  2016-08-19       Impact factor: 4.354

5.  Copper-Catalyzed 1,2-Amino Oxygenation of 1,3-Dienes: A Chemo-, Regio-, and Site-Selective Three-Component Reaction with O-Acylhydroxylamines and Carboxylic Acids.

Authors:  Brett N Hemric; Andy W Chen; Qiu Wang
Journal:  ACS Catal       Date:  2019-09-24       Impact factor: 13.084

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

Authors:  Vaneet Saini; Longyan Liao; Qiaofeng Wang; Ranjan Jana; Matthew S Sigman
Journal:  Org Lett       Date:  2013-09-18       Impact factor: 6.005

7.  An Expedient Route to 9-arylmethylanthracene Derivatives via Tandem Ni-catalyzed Alkene Dicarbofunctionalization and Acid-promoted Cyclization-aromatization.

Authors:  Doleshwar Niroula; Rishi R Sapkota; Roshan K Dhungana; Bijay Shrestha; Ramesh Giri
Journal:  Isr J Chem       Date:  2020-02-14       Impact factor: 3.333

8.  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

9.  A Diverted Aerobic Heck Reaction Enables Selective 1,3-Diene and 1,3,5-Triene Synthesis through C-C Bond Scission.

Authors:  Neil J McAlpine; Long Wang; Brad P Carrow
Journal:  J Am Chem Soc       Date:  2018-10-15       Impact factor: 15.419

10.  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
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