Literature DB >> 21469713

Rhodium-catalyzed selective olefination of arene esters via C-H bond activation.

Sae Hume Park1, Ji Young Kim, Sukbok Chang.   

Abstract

A new catalytic procedure of ortho-olefination of benzoates and benzaldehydes has been developed. Ester and carboxaldehyde units were revealed to be effective chelating groups in focusing the activation of aryl C-H bonds ortho to the directing moieties under the Rh-catalyzed oxidative conditions. The reaction is highly regioselective with a range of benzoates and benzaldehydes enabling the efficient olefination with acrylates, acrylic acid, and styrenes.

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Year:  2011        PMID: 21469713     DOI: 10.1021/ol200600p

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


  15 in total

1.  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

2.  Ether-directed ortho-C-H olefination with a palladium(II)/monoprotected amino acid catalyst.

Authors:  Gang Li; Dasheng Leow; Li Wan; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2012-12-13       Impact factor: 15.336

3.  Activation of remote meta-C-H bonds assisted by an end-on template.

Authors:  Dasheng Leow; Gang Li; Tian-Sheng Mei; Jin-Quan Yu
Journal:  Nature       Date:  2012-06-27       Impact factor: 49.962

4.  Meta-selective C-H functionalization using a nitrile-based directing group and cleavable Si-tether.

Authors:  Sunggi Lee; Hyelee Lee; Kian L Tan
Journal:  J Am Chem Soc       Date:  2013-12-10       Impact factor: 15.419

5.  Pd(II)-catalyzed C-H functionalizations directed by distal weakly coordinating functional groups.

Authors:  Gang Li; Li Wan; Guofu Zhang; Dasheng Leow; Jillian Spangler; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2015-03-24       Impact factor: 15.419

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.  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

9.  Ligand-enabled cross-coupling of C(sp3)-H bonds with arylboron reagents via Pd(II)/Pd(0) catalysis.

Authors:  Kelvin S L Chan; Masayuki Wasa; Ling Chu; Brian N Laforteza; Masanori Miura; Jin-Quan Yu
Journal:  Nat Chem       Date:  2014-01-05       Impact factor: 24.427

10.  Conformation-induced remote meta-C-H activation of amines.

Authors:  Ri-Yuan Tang; Gang Li; Jin-Quan Yu
Journal:  Nature       Date:  2014-03-13       Impact factor: 49.962

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