Literature DB >> 17057865

5-endo Heck-type cyclization of 2-(trifluoromethyl)allyl ketone oximes: Synthesis of 4-difluoromethylene-substituted 1-pyrrolines.

Junji Ichikawa1, Ryo Nadano, Naotaka Ito.   

Abstract

2-(Trifluoromethyl)allyl ketone O-pentafluorobenzoyloximes undergo a palladium-catalyzed 5-endo mode of alkene insertion via oxidative addition of the N-O bond, followed by beta-fluorine elimination to produce 4-difluoromethylene-1-pyrrolines.

Entities:  

Year:  2006        PMID： 17057865     DOI： 10.1039/b610690k

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  9 in total

Review 1.  Cross-Coupling of Heteroatomic Electrophiles.

Authors:  Katerina M Korch; Donald A Watson
Journal:  Chem Rev       Date:  2019-06-11       Impact factor: 60.622

2.  Synthesis of N-H Bearing Imidazolidinones and Dihydroimidazolones Using Aza-Heck Cyclizations.

Authors:  Feiyang Xu; Scott A Shuler; Donald A Watson
Journal:  Angew Chem Int Ed Engl       Date:  2018-08-19       Impact factor: 15.336

3.  Activation of diverse carbon-heteroatom and carbon-carbon bonds via palladium(II)-catalysed β-X elimination.

Authors:  Van T Tran; John A Gurak; Kin S Yang; Keary M Engle
Journal:  Nat Chem       Date:  2018-08-20       Impact factor: 24.427

4.  Synthesis of Indolines and Derivatives by Aza-Heck Cyclization.

Authors:  Feiyang Xu; Katerina M Korch; Donald A Watson
Journal:  Angew Chem Int Ed Engl       Date:  2019-08-13       Impact factor: 15.336

5.  Heck-like Reactions Involving Heteroatomic Electrophiles.

Authors:  Bojan Vulovic; Donald A Watson
Journal:  European J Org Chem       Date:  2017-07-05

6.  Palladium-Catalyzed Defluorinative Coupling of 1-Aryl-2,2-Difluoroalkenes and Boronic Acids: Stereoselective Synthesis of Monofluorostilbenes.

Authors:  Richard T Thornbury; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2016-08-11       Impact factor: 15.336

7.  Rhodium-catalysed C(sp(2))-C(sp(2)) bond formation via C-H/C-F activation.

Authors:  Panpan Tian; Chao Feng; Teck-Peng Loh
Journal:  Nat Commun       Date:  2015-06-17       Impact factor: 14.919

8.  Recent developments in the use of aza-Heck cyclizations for the synthesis of chiral N-heterocycles.

Authors:  Nicholas J Race; Ian R Hazelden; Adele Faulkner; John F Bower
Journal:  Chem Sci       Date:  2017-06-20       Impact factor: 9.825

9.  Tandem aza-Heck Suzuki and carbonylation reactions of O-phenyl hydroxamic ethers: complex lactams via carboamination.

Authors:  Run-Duo Gao; Scott A Shuler; Donald A Watson
Journal:  Chem Sci       Date:  2021-05-27       Impact factor: 9.825
  9 in total

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