Literature DB >> 21175143

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

Andy S Tsai1, Mikaël Brasse, Robert G Bergman, Jonathan A Ellman.   

Abstract

Oxime directed aromatic C-H bond activation and oxidative coupling to alkenes is reported using a cationic Rh(III) catalyst. Significantly, the method can be used to oxidatively couple unactivated, aliphatic alkenes.

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Year:  2010        PMID： 21175143      PMCID： PMC3031716          DOI： 10.1021/ol102890k

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


  30 in total

1.  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

2.  Rh(III)-catalyzed oxidative coupling of N-aryl-2-aminopyridine with alkynes and alkenes.

Authors:  Jinlei Chen; Guoyong Song; Cheng-Ling Pan; Xingwei Li
Journal:  Org Lett       Date:  2010-11-01       Impact factor: 6.005

3.  Oxidative coupling of aromatic substrates with alkynes and alkenes under rhodium catalysis.

Authors:  Tetsuya Satoh; Masahiro Miura
Journal:  Chemistry       Date:  2010-10-04       Impact factor: 5.236

4.  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

5.  Cycloisomerization of 1,6-enynes using acetate as a nucleophile under palladium(II) catalysis.

Authors:  Qinghai Zhang; Wei Xu; Xiyan Lu
Journal:  J Org Chem       Date:  2005-02-18       Impact factor: 4.354

6.  Constructing multiply substituted arenes using sequential palladium(II)-catalyzed C-H olefination.

Authors:  Keary M Engle; Dong-Hui Wang; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2010-08-16       Impact factor: 15.336

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

Authors:  Eric M Ferreira; Haiming Zhang; Brian M Stoltz
Journal:  Tetrahedron       Date:  2008-06-23       Impact factor: 2.457

8.  Palladium-catalyzed C-H functionalization of pyridine N-oxides: highly selective alkenylation and direct arylation with unactivated arenes.

Authors:  Seung Hwan Cho; Seung Jun Hwang; Sukbok Chang
Journal:  J Am Chem Soc       Date:  2008-06-27       Impact factor: 15.419

9.  Rhodium-catalyzed mono- and divinylation of 1-phenylpyrazoles and related compounds via regioselective C-H bond cleavage.

Authors:  Nobuyoshi Umeda; Koji Hirano; Tetsuya Satoh; Masahiro Miura
Journal:  J Org Chem       Date:  2009-09-18       Impact factor: 4.354

10.  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
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  22 in total

1.  Rhodium catalyzed chelation-assisted C-H bond functionalization reactions.

Authors:  Denise A Colby; Andy S Tsai; Robert G Bergman; Jonathan A Ellman
Journal:  Acc Chem Res       Date:  2011-12-08       Impact factor: 22.384

2.  Scope and Mechanistic Study of the Coupling Reaction of α, β-Unsaturated Carbonyl Compounds with Alkenes: Uncovering Electronic Effects on Alkene Insertion vs Oxidative Coupling Pathways.

Authors:  Ki-Hyeok Kwon; Do W Lee; Chae S Yi
Journal:  Organometallics       Date:  2012-01-09       Impact factor: 3.876

3.  Pyridine synthesis from oximes and alkynes via rhodium(III) catalysis: Cp* and Cp(t) provide complementary selectivity.

Authors:  Todd K Hyster; Tomislav Rovis
Journal:  Chem Commun (Camb)       Date:  2011-10-10       Impact factor: 6.222

4.  Rhodium(iii)-catalyzed synthesis of phthalides by cascade addition and cyclization of benzimidates with aldehydes.

Authors:  Yajing Lian; Robert G Bergman; Jonathan A Ellman
Journal:  Chem Sci       Date:  2012-08-02       Impact factor: 9.825

5.  Complementary regioselectivity in Rh(III)-catalyzed insertions of potassium vinyltrifluoroborate via C-H activation: preparation and use of 4-trifluoroboratotetrahydroisoquinolones.

Authors:  Marc Presset; Daniel Oehlrich; Frederik Rombouts; Gary A Molander
Journal:  Org Lett       Date:  2013-03-15       Impact factor: 6.005

6.  Rh(III)-catalyzed regioselective synthesis of pyridines from alkenes and α,β-unsaturated oxime esters.

Authors:  Jamie M Neely; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2012-12-18       Impact factor: 15.419

7.  Mechanistic study of the oxidative coupling of styrene with 2-phenylpyridine derivatives catalyzed by cationic rhodium(III) via C-H activation.

Authors:  Mikaël Brasse; Juan Cámpora; Jonathan A Ellman; Robert G Bergman
Journal:  J Am Chem Soc       Date:  2013-04-16       Impact factor: 15.419

8.  Convergent Synthesis of Diverse Nitrogen Heterocycles via Rh(III)-Catalyzed C-H Conjugate Addition/Cyclization Reactions.

Authors:  Adam B Weinstein; Jonathan A Ellman
Journal:  Org Lett       Date:  2016-06-23       Impact factor: 6.005

9.  Copper-catalyzed oxidative Heck reactions between alkyltrifluoroborates and vinyl arenes.

Authors:  Timothy W Liwosz; Sherry R Chemler
Journal:  Org Lett       Date:  2013-06-04       Impact factor: 6.005

10.  Rhodium(III)-catalyzed alkenyl C-H bond functionalization: convergent synthesis of furans and pyrroles.

Authors:  Yajing Lian; Tatjana Huber; Kevin D Hesp; Robert G Bergman; Jonathan A Ellman
Journal:  Angew Chem Int Ed Engl       Date:  2012-11-22       Impact factor: 15.336
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