Literature DB >> 24504659

Ligand-controlled α- and β-arylation of acyclic N-Boc amines.

Anthony Millet1, David Dailler, Paolo Larini, Olivier Baudoin.   

Abstract

The palladium-catalyzed ligand-controlled arylation of α-zincated acyclic amines, obtained by directed α-lithiation and transmetalation, is described. Whereas PtBu3 gave rise to α-arylated Boc-protected amines, more flexible N-phenylazole-based phosphine ligands induced major β-arylation through migrative cross-coupling.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CC coupling; arylation; cross-coupling; density functional calculations; palladium

Mesh：

Substances：

Year:  2014        PMID： 24504659     DOI： 10.1002/anie.201310904

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  9 in total

1.  Palladium-catalyzed C(sp(3))-H Arylation of N-Boc benzylalkylamines via a deprotonative cross-coupling process.

Authors:  Nusrah Hussain; Byeong-Seon Kim; Patrick J Walsh
Journal:  Chemistry       Date:  2015-06-30       Impact factor: 5.236

2.  Tandem C(sp3)-H Arylation/Oxidation and Arylation/Allylic Substitution of Isoindolinones.

Authors:  Jacqueline Jiménez; Byeong-Seon Kim; Patrick J Walsh
Journal:  Adv Synth Catal       Date:  2016-08-02       Impact factor: 5.837

3.  Palladium-Catalyzed Pyrazole-Directed sp3 C-H Bond Arylation for the Synthesis of β-Phenethylamines.

Authors:  Nurbey Gulia; Olafs Daugulis
Journal:  Angew Chem Int Ed Engl       Date:  2017-02-24       Impact factor: 15.336

4.  β-Functionalization of Saturated Aza-Heterocycles Enabled by Organic Photoredox Catalysis.

Authors:  Natalie Holmberg-Douglas; Younggi Choi; Brian Aquila; Hoan Huynh; David A Nicewicz
Journal:  ACS Catal       Date:  2021-02-24       Impact factor: 13.700

5.  Palladium-Catalyzed Benzylic C-H Arylation of Azaarylmethylamines.

Authors:  Byeong-Seon Kim; Jacqueline Jiménez; Feng Gao; Patrick J Walsh
Journal:  Org Lett       Date:  2015-11-17       Impact factor: 6.005

6.  Chain Walking of Allylrhodium Species Towards Esters During Rhodium-Catalyzed Nucleophilic Allylations of Imines.

Authors:  Jose I Martínez; Joshua J Smith; Hamish B Hepburn; Hon Wai Lam
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-03       Impact factor: 15.336

7.  β-Arylation of oxime ethers using diaryliodonium salts through activation of inert C(sp)-H bonds using a palladium catalyst.

Authors:  Jing Peng; Chao Chen; Chanjuan Xi
Journal:  Chem Sci       Date:  2015-11-11       Impact factor: 9.825

8.  Phosphoric acid-catalyzed atroposelective construction of axially chiral arylpyrroles.

Authors:  Lei Zhang; Shao-Hua Xiang; Jun Joelle Wang; Jian Xiao; Jun-Qi Wang; Bin Tan
Journal:  Nat Commun       Date:  2019-02-04       Impact factor: 14.919

9.  Regiodivergent enantioselective C-H functionalization of Boc-1,3-oxazinanes and application to the synthesis of β2 and β3-amino acids.

Authors:  Weilong Lin; Ke-Feng Zhang; Olivier Baudoin
Journal:  Nat Catal       Date:  2019-09-09
  9 in total

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