Literature DB >> 23473452

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

Matthew S McCammant1, Longyan Liao, Matthew S Sigman.   

Abstract

A palladium-catalyzed 1,4-addition across the commodity chemical 1,3-butadiene to afford skipped polyene products is reported. Through a palladium σ → π → σ allyl isomerization, two new carbon-carbon bonds are formed with high regioselectivity and trans stereoselectivity of the newly formed alkene. The utility of this method is highlighted by the successful synthesis of the ripostatin A skipped triene core.

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Year:  2013        PMID： 23473452      PMCID： PMC3688275          DOI： 10.1021/ja3110544

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


  53 in total

1.  Palladium-catalyzed hydrofunctionalization of vinyl phenol derivatives with heteroaromatics.

Authors:  Tejas P Pathak; Matthew S Sigman
Journal:  Org Lett       Date:  2011-04-21       Impact factor: 6.005

2.  Total synthesis of RNA-polymerase inhibitor ripostatin B and 15-deoxyripostatin A.

Authors:  Wufeng Tang; Evgeny V Prusov
Journal:  Angew Chem Int Ed Engl       Date:  2012-02-29       Impact factor: 15.336

3.  Total synthesis of piericidin A1 and B1 and key analogues.

Authors:  Martin J Schnermann; F Anthony Romero; Inkyu Hwang; Eiko Nakamaru-Ogiso; Takao Yagi; Dale L Boger
Journal:  J Am Chem Soc       Date:  2006-09-13       Impact factor: 15.419

4.  Total synthesis of jerangolid D.

Authors:  Jirí Pospísil; Istvan E Markó
Journal:  J Am Chem Soc       Date:  2007-02-23       Impact factor: 15.419

5.  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

6.  Total synthesis of lehualide B by allylic alcohol-alkyne reductive cross-coupling.

Authors:  Valer Jeso; Glenn C Micalizio
Journal:  J Am Chem Soc       Date:  2010-08-25       Impact factor: 15.419

7.  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

8.  The jerangolids: A family of new antifungal compounds from Sorangium cellulosum (Myxobacteria). Production, physico-chemical and biological properties of jerangolid A.

Authors:  K Gerth; P Washausen; G Hofle; H Irschik; H Reichenbach
Journal:  J Antibiot (Tokyo)       Date:  1996-01       Impact factor: 2.649

9.  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

10.  Iridium-catalyzed allylic vinylation and asymmetric allylic amination reactions with o-aminostyrenes.

Authors:  Ke-Yin Ye; Hu He; Wen-Bo Liu; Li-Xin Dai; Günter Helmchen; Shu-Li You
Journal:  J Am Chem Soc       Date:  2011-11-02       Impact factor: 15.419
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  18 in total

1.  Catalytic conjunctive cross-coupling enabled by metal-induced metallate rearrangement.

Authors:  Liang Zhang; Gabriel J Lovinger; Emma K Edelstein; Adam A Szymaniak; Matteo P Chierchia; James P Morken
Journal:  Science       Date:  2016-01-01       Impact factor: 47.728

2.  Allylic functionalization of unactivated olefins with Grignard reagents.

Authors:  Hongli Bao; Liela Bayeh; Uttam K Tambar
Journal:  Angew Chem Int Ed Engl       Date:  2014-01-23       Impact factor: 15.336

3.  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

4.  Palladium-Catalyzed 1,3-Difunctionalization Using Terminal Alkenes with Alkenyl Nonaflates and Aryl Boronic Acids.

Authors:  Matthew S McCammant; Takashi Shigeta; Matthew S Sigman
Journal:  Org Lett       Date:  2016-03-28       Impact factor: 6.005

5.  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

6.  Palladium-catalyzed enantioselective Heck alkenylation of acyclic alkenols using a redox-relay strategy.

Authors:  Harshkumar H Patel; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2015-03-09       Impact factor: 15.419

7.  Nickel-Catalyzed Stereoselective Diarylation of Alkenylarenes.

Authors:  Pin Gao; Liang-An Chen; M Kevin Brown
Journal:  J Am Chem Soc       Date:  2018-08-20       Impact factor: 15.419

Review 8.  Alkynes as Electrophilic or Nucleophilic Allylmetal Precursors in Transition-Metal Catalysis.

Authors:  Alexander M Haydl; Bernhard Breit; Tao Liang; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-10       Impact factor: 15.336

9.  Rhodium-Catalyzed Hydrofunctionalization: Enantioselective Coupling of Indolines and 1,3-Dienes.

Authors:  Xiao-Hui Yang; Vy M Dong
Journal:  J Am Chem Soc       Date:  2017-01-27       Impact factor: 15.419

10.  Oxidative Heck vinylation for the synthesis of complex dienes and polyenes.

Authors:  Jared H Delcamp; Paul E Gormisky; M Christina White
Journal:  J Am Chem Soc       Date:  2013-05-30       Impact factor: 15.419
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