Literature DB >> 25873526

Palladium(0)/PAr3 -Catalyzed Intermolecular Amination of C(sp(3) )H Bonds: Synthesis of β-Amino Acids.

Jian He1, Toshihiko Shigenari1, Jin-Quan Yu2.   

Abstract

An intermolecular C(sp(3))-H amination using a Pd(0) /PAr3 catalyst was developed. The reaction begins with oxidative addition of R2 N-OBz to a Pd(0) /PAr3 catalyst and subsequent cleavage of a C(sp(3))-H bond by the generated Pd-NR2 intermediate. The catalytic cycle proceeds without the need for external oxidants in a similar manner to the extensively studied palladium(0)-catalyzed C-H arylation reactions. The electron-deficient triarylphosphine ligand is crucial for this C(sp(3))-H amination reaction to occur.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CH activation; amination; amino acids; palladium; synthetic methods

Mesh:

Substances:

Year:  2015        PMID: 25873526     DOI: 10.1002/anie.201502075

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


  15 in total

1.  Palladium-Catalyzed Transformations of Alkyl C-H Bonds.

Authors:  Jian He; Masayuki Wasa; Kelvin S L Chan; Qian Shao; Jin-Quan Yu
Journal:  Chem Rev       Date:  2016-12-02       Impact factor: 60.622

Review 2.  Complementary Strategies for Directed C(sp3 )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

Authors:  John C K Chu; Tomislav Rovis
Journal:  Angew Chem Int Ed Engl       Date:  2017-12-05       Impact factor: 15.336

Review 3.  Cross-Coupling of Heteroatomic Electrophiles.

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

4.  Pd-Catalyzed Alkene Diamination Reactions of Nitrogen Electrophiles: Synthesis of Cyclic Guanidines and Ureas Bearing Dialkylaminomethyl Groups.

Authors:  Luke J Peterson; Janelle K Kirsch; John P Wolfe
Journal:  Org Lett       Date:  2018-06-06       Impact factor: 6.005

5.  Ligand-Promoted meta-C-H Amination and Alkynylation.

Authors:  Peng Wang; Gen-Cheng Li; Pankaj Jain; Marcus E Farmer; Jian He; Peng-Xiang Shen; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2016-10-13       Impact factor: 15.419

Review 6.  Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp3)-H Bonds.

Authors:  Bin Liu; Andrew M Romine; Camille Z Rubel; Keary M Engle; Bing-Feng Shi
Journal:  Chem Rev       Date:  2021-10-29       Impact factor: 60.622

7.  Palladium-Catalyzed Enantioselective β-C(sp3)-H Activation Reactions of Aliphatic Acids: A Retrosynthetic Surrogate for Enolate Alkylation and Conjugate Addition.

Authors:  Erika L Lucas; Nelson Y S Lam; Zhe Zhuang; Hau Sun Sam Chan; Daniel A Strassfeld; Jin-Quan Yu
Journal:  Acc Chem Res       Date:  2022-01-25       Impact factor: 24.466

8.  Modular ipso/ ortho Difunctionalization of Aryl Bromides via Palladium/Norbornene Cooperative Catalysis.

Authors:  Zhe Dong; Gang Lu; Jianchun Wang; Peng Liu; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2018-06-27       Impact factor: 15.419

9.  Rh(iii)-catalyzed tandem annulative redox-neutral arylation/amidation of aromatic tethered alkenes.

Authors:  Chao Chen; Chen Shi; Yaxi Yang; Bing Zhou
Journal:  Chem Sci       Date:  2020-10-16       Impact factor: 9.825

10.  Diverse N-Heterocyclic Ring Systems via Aza-Heck Cyclizations of N-(Pentafluorobenzoyloxy)sulfonamides.

Authors:  Ian R Hazelden; Xiaofeng Ma; Thomas Langer; John F Bower
Journal:  Angew Chem Int Ed Engl       Date:  2016-07-27       Impact factor: 15.336

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.