Literature DB >> 18587498

C-H Bond Functionalizations with Palladium(II): Intramolecular Oxidative Annulations of Arenes.

Eric M Ferreira1, Haiming Zhang, Brian M Stoltz.   

Abstract

Oxidative annulations for the synthesis of carbocycles were developed using a catalytic palladium(II) system. Indoles with pendant olefin tethers were oxidatively cyclized to form annulated products. Electron-rich aromatic systems were also investigated, culminating in the synthesis of benzofurans and dihydrobenzofurans by a similar protocol. These reactions were demonstrated to proceed by an initial C-H bond functionalization event, followed by olefin insertion and β-hydride elimination.

Entities:  

Year:  2008        PMID： 18587498      PMCID： PMC2441596          DOI： 10.1016/j.tet.2008.01.052

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  33 in total

1.  Ru-, Rh-, and Pd-catalyzed C-C bond formation involving C-H activation and addition on unsaturated substrates: reactions and mechanistic aspects.

Authors:  Vincent Ritleng; Claude Sirlin; Michel Pfeffer
Journal:  Chem Rev       Date:  2002-05       Impact factor: 60.622

2.  The asymmetric intramolecular Heck reaction in natural product total synthesis.

Authors:  Amy B Dounay; Larry E Overman
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

3.  The total synthesis of (+)-dragmacidin F.

Authors:  Neil K Garg; Daniel D Caspi; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2004-08-11       Impact factor: 15.419

4.  Direct oxidative Heck cyclizations: intramolecular Fujiwara-Moritani arylations for the synthesis of functionalized benzofurans and dihydrobenzofurans.

Authors:  Haiming Zhang; Eric M Ferreira; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2004-11-19       Impact factor: 15.336

5.  Tremorgenic toxin from Penicillium cyclopium grown on food materials.

Authors:  B J Wilson; C H Wilson; A W Hayes
Journal:  Nature       Date:  1968-10-05       Impact factor: 49.962

6.  Selective Pd-catalyzed oxidative coupling of anilides with olefins through C-H bond activation at room temperature.

Authors:  Maarten D K Boele; Gino P F van Strijdonck; André H M de Vries; Paul C J Kamer; Johannes G de Vries; Piet W N M van Leeuwen
Journal:  J Am Chem Soc       Date:  2002-02-27       Impact factor: 15.419

7.  A short synthetic route to (+)-austamide, (+)-deoxyisoaustamide, and (+)-hydratoaustamide from a common precursor by a novel palladium-mediated indole --> dihydroindoloazocine cyclization.

Authors:  Phil S Baran; E J Corey
Journal:  J Am Chem Soc       Date:  2002-07-10       Impact factor: 15.419

Review 8.  Palladium oxidase catalysis: selective oxidation of organic chemicals by direct dioxygen-coupled turnover.

Authors:  Shannon S Stahl
Journal:  Angew Chem Int Ed Engl       Date:  2004-06-28       Impact factor: 15.336

9.  Direct coupling of benzene with olefin catalyzed by Pd(OAc)(2) combined with heteropolyoxometalate under dioxygen.

Authors:  Takahiro Yokota; Masayuki Tani; Satoshi Sakaguchi; Yasutaka Ishii
Journal:  J Am Chem Soc       Date:  2003-02-12       Impact factor: 15.419

10.  Platinum-catalyzed intramolecular alkylation of indoles with unactivated olefins.

Authors:  Cong Liu; Xiaoqing Han; Xiang Wang; Ross A Widenhoefer
Journal:  J Am Chem Soc       Date:  2004-03-31       Impact factor: 15.419
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  7 in total

1.  Twofold C-H functionalization: palladium-catalyzed ortho arylation of anilides.

Authors:  Gordon Brasche; Jorge García-Fortanet; Stephen L Buchwald
Journal:  Org Lett       Date:  2008-05-09       Impact factor: 6.005

2.  Rh(III)-catalyzed oxidative coupling of unactivated alkenes via C-H activation.

Authors:  Andy S Tsai; Mikaël Brasse; Robert G Bergman; Jonathan A Ellman
Journal:  Org Lett       Date:  2010-12-22       Impact factor: 6.005

Review 3.  Palladium(II)-catalyzed alkene functionalization via nucleopalladation: stereochemical pathways and enantioselective catalytic applications.

Authors:  Richard I McDonald; Guosheng Liu; Shannon S Stahl
Journal:  Chem Rev       Date:  2011-03-23       Impact factor: 60.622

4.  Direct, chemoselective N-tert-prenylation of indoles by C-H functionalization.

Authors:  Michael R Luzung; Chad A Lewis; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

5.  Efficient Microwave-assisted One-pot Three-component Synthesis of 2,3-Disubstituted Benzofurans under Sonogashira Conditions.

Authors:  Nataliya A Markina; Yu Chen; Richard C Larock
Journal:  Tetrahedron       Date:  2013-04       Impact factor: 2.457

6.  Highly Efficient Cascade Reaction for Selective Formation of Spirocyclobutenes from Dienallenes via Palladium-Catalyzed Oxidative Double Carbocyclization-Carbonylation-Alkynylation.

Authors:  Youai Qiu; Bin Yang; Can Zhu; Jan-E Bäckvall
Journal:  J Am Chem Soc       Date:  2016-10-13       Impact factor: 15.419

7.  Palladium-catalyzed dual C-H or N-H functionalization of unfunctionalized indole derivatives with alkenes and arenes.

Authors:  Gianluigi Broggini; Egle M Beccalli; Andrea Fasana; Silvia Gazzola
Journal:  Beilstein J Org Chem       Date:  2012-10-11       Impact factor: 2.883
  7 in total

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