Literature DB >> 20481606

Pd(II)-catalyzed oxidative 1,1-diarylation of terminal olefins.

Erik W Werner1, Kaveri B Urkalan, Matthew S Sigman.   

Abstract

Evaluation of the scope of a Pd(II)-catalyzed oxidative 1,1-diarylation reaction of terminal olefins using aryl stannanes is reported. The reaction is shown to be tolerant of functionality commonly encountered in organic synthesis; however, the reaction outcome was found to be dependent on the nature of the aryl stannane used. A mechanistic rationale for the observation of this influence is provided.

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Year:  2010        PMID： 20481606      PMCID： PMC2908953          DOI： 10.1021/ol1009575

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


  43 in total

1.  A new asymmetric Wacker-type cyclization and tandem cyclization promoted by Pd(II)-spiro bis(isoxazoline) catalyst.

Authors:  M A Arai; M Kuraishi; T Arai; H Sasai
Journal:  J Am Chem Soc       Date:  2001-03-28       Impact factor: 15.419

2.  Construction of tetrahydrofurans by PdII/PdIV-catalyzed aminooxygenation of alkenes.

Authors:  Lopa V Desai; Melanie S Sanford
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

3.  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

4.  A facile Pd(0)-catalyzed regio- and stereoselective diamination of conjugated dienes and trienes.

Authors:  Haifeng Du; Baoguo Zhao; Yian Shi
Journal:  J Am Chem Soc       Date:  2007-01-31       Impact factor: 15.419

5.  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

6.  Oxidative palladium(II) catalysis: A highly efficient and chemoselective cross-coupling method for carbon-carbon bond formation under base-free and nitrogenous-ligand conditions.

Authors:  Kyung Soo Yoo; Cheol Hwan Yoon; Rajesh K Mishra; Young Chun Jung; Sung Wook Yi; Kyung Woon Jung
Journal:  J Am Chem Soc       Date:  2006-12-20       Impact factor: 15.419

7.  New phenylpropenoids, bis(1-phenylethyl)phenols, bisquinolinone alkaloid, and anti-inflammatory constituents from Zanthoxylum integrifoliolum.

Authors:  Jih-Jung Chen; Po-Hou Chen; Chang-Hui Liao; Shi-Yu Huang; Ih-Sheng Chen
Journal:  J Nat Prod       Date:  2007-09-07       Impact factor: 4.050

8.  Chiral N-heterocyclic carbene--Pd(0)-catalyzed asymmetric diamination of conjugated dienes and triene.

Authors:  Liang Xu; Yian Shi
Journal:  J Org Chem       Date:  2007-12-21       Impact factor: 4.354

9.  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

10.  Pd(II)-catalyzed enantioselective oxidative tandem cyclization reactions. Synthesis of indolines through C-N and C-C bond formation.

Authors:  Kai-Tai Yip; Min Yang; Ka-Lun Law; Nian-Yong Zhu; Dan Yang
Journal:  J Am Chem Soc       Date:  2006-03-15       Impact factor: 15.419
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  23 in total

1.  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

2.  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

3.  Imparting catalyst control upon classical palladium-catalyzed alkenyl C-H bond functionalization reactions.

Authors:  Matthew S Sigman; Erik W Werner
Journal:  Acc Chem Res       Date:  2011-11-23       Impact factor: 22.384

4.  Asymmetric palladium-catalyzed hydroarylation of styrenes and dienes.

Authors:  Susanne M Podhajsky; Yasumasa Iwai; Amanda Cook-Sneathen; Matthew S Sigman
Journal:  Tetrahedron       Date:  2011-06-17       Impact factor: 2.457

5.  Alternative pathways for Heck intermediates: palladium-catalyzed oxyarylation of homoallylic alcohols.

Authors:  Chen Zhu; John R Falck
Journal:  Angew Chem Int Ed Engl       Date:  2011-06-08       Impact factor: 15.336

6.  Nickel-Catalyzed α-Carbonylalkylarylation of Vinylarenes: Expedient Access to γ,γ-Diarylcarbonyl and Aryltetralone Derivatives.

Authors:  Shekhar Kc; Roshan K Dhungana; Namrata Khanal; Ramesh Giri
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-19       Impact factor: 15.336

7.  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

8.  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

9.  Palladium-catalyzed allylic cross-coupling reactions of primary and secondary homoallylic electrophiles.

Authors:  Benjamin J Stokes; Susanne M Opra; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2012-07-06       Impact factor: 15.419

10.  Scope and mechanism of the Pt-catalyzed enantioselective diboration of monosubstituted alkenes.

Authors:  John R Coombs; Fredrik Haeffner; Laura T Kliman; James P Morken
Journal:  J Am Chem Soc       Date:  2013-07-18       Impact factor: 15.419
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