Literature DB >> 24579653

Competition between sp³-C-N vs sp³-C-F reductive elimination from Pd(IV) complexes.

Mónica H Pérez-Temprano1, Joy M Racowski, Jeff W Kampf, Melanie S Sanford.   

Abstract

This communication describes the design of a model system that allows direct investigation of competing sp(3)-C-N and sp(3)-C-F bond-forming reductive elimination from a Pd(IV) fluoro sulfonamide complex. The reductive elimination selectivity varies dramatically as a function of reaction additives. A mechanism is proposed that provides a rationale for these effects.

Entities:  

Year:  2014        PMID： 24579653     DOI： 10.1021/ja411433f

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


  11 in total

1.  Ligand-Enabled Stereoselective β-C(sp(3))-H Fluorination: Synthesis of Unnatural Enantiopure anti-β-Fluoro-α-amino Acids.

Authors:  Ru-Yi Zhu; Keita Tanaka; Gen-Cheng Li; Jian He; Hai-Yan Fu; Su-Hua Li; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2015-05-27       Impact factor: 15.419

2.  A Neophyl Palladacycle as an Air- and Thermally Stable Precursor to Oxidative Addition Complexes.

Authors:  Ryan P King; Shane W Krska; Stephen L Buchwald
Journal:  Org Lett       Date:  2021-10-06       Impact factor: 6.072

3.  Halide-Dependent Mechanisms of Reductive Elimination from Gold(III).

Authors:  Matthew S Winston; William J Wolf; F Dean Toste
Journal:  J Am Chem Soc       Date:  2015-06-11       Impact factor: 15.419

4.  Palladium-catalyzed enantioselective 1,1-fluoroarylation of aminoalkenes.

Authors:  Ying He; Zhenyu Yang; Richard T Thornbury; F Dean Toste
Journal:  J Am Chem Soc       Date:  2015-09-17       Impact factor: 15.419

5.  Studying regioisomer formation in the Pd-catalyzed fluorination of aryl triflates by deuterium labeling.

Authors:  Phillip J Milner; Tom Kinzel; Yong Zhang; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2014-10-21       Impact factor: 15.419

6.  Methylpalladium complexes with pyrimidine-functionalized N-heterocyclic carbene ligands.

Authors:  Dirk Meyer; Thomas Strassner
Journal:  Beilstein J Org Chem       Date:  2016-07-21       Impact factor: 2.883

7.  Aryl C(sp2)-X Coupling (X = C, N, O, Cl) and Facile Control of N-Mono- and N,N-Diarylation of Primary Alkylamines at a Pt(IV) Center.

Authors:  Xiaoxi Lin; Arkadi Vigalok; Andrei N Vedernikov
Journal:  J Am Chem Soc       Date:  2020-11-23       Impact factor: 15.419

8.  Anion-Dependent Switch in C-X Reductive Elimination Diastereoselectivity.

Authors:  Michael J Geier; Marzieh Dadkhah Aseman; Michel R Gagné
Journal:  Organometallics       Date:  2014-08-14       Impact factor: 3.876

9.  A Fluorinated Ligand Enables Room-Temperature and Regioselective Pd-Catalyzed Fluorination of Aryl Triflates and Bromides.

Authors:  Aaron C Sather; Hong Geun Lee; Valentina Y De La Rosa; Yang Yang; Peter Müller; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2015-10-06       Impact factor: 15.419

10.  Controlling Pd(IV) reductive elimination pathways enables Pd(II)-catalysed enantioselective C(sp3)-H fluorination.

Authors:  Hojoon Park; Pritha Verma; Kai Hong; Jin-Quan Yu
Journal:  Nat Chem       Date:  2018-06-11       Impact factor: 24.427
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