Literature DB >> 22059931

Ligand-promoted C3-selective arylation of pyridines with Pd catalysts: gram-scale synthesis of (±)-preclamol.

Mengchun Ye1, Guo-Lin Gao, Andrew J F Edmunds, P A Worthington, James A Morris, Jin-Quan Yu.   

Abstract

The first example of Pd-catalyzed, C3-selective arylation of unprotected pyridines has been developed by employing a catalytic system consisting of Pd(OAc)(2) and 1,10-phenanthroline. This protocol provides an expeditious route to an important class of 3-arylpyridines and 3-arylpiperidines frequently found in bioactive compounds. A brief synthesis of the drug molecule (±)-preclamol is also reported.

Entities:  

Mesh：

Substances：

Year:  2011        PMID： 22059931     DOI： 10.1021/ja209510q

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


  16 in total

1.  A meta-selective C-H borylation directed by a secondary interaction between ligand and substrate.

Authors:  Yoichiro Kuninobu; Haruka Ida; Mitsumi Nishi; Motomu Kanai
Journal:  Nat Chem       Date:  2015-08-17       Impact factor: 24.427

2.  Pd(II)-catalyzed C-H iodination using molecular I2 as the sole oxidant.

Authors:  Xiao-Chen Wang; Yi Hu; Samuel Bonacorsi; Yang Hong; Richard Burrell; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2013-07-09       Impact factor: 15.419

3.  C-H bonds as ubiquitous functionality: preparation of multiple regioisomers of arylated 1,2,4-triazoles via C-H arylation.

Authors:  Jung Min Joo; Pengfei Guo; Dalibor Sames
Journal:  J Org Chem       Date:  2012-12-31       Impact factor: 4.354

4.  Radical-based regioselective C-H functionalization of electron-deficient heteroarenes: scope, tunability, and predictability.

Authors:  Fionn O'Hara; Donna G Blackmond; Phil S Baran
Journal:  J Am Chem Soc       Date:  2013-07-30       Impact factor: 15.419

5.  Recent Advances in the C-H-Functionalization of the Distal Positions in Pyridines and Quinolines.

Authors:  David E Stephens; Oleg V Larionov
Journal:  Tetrahedron       Date:  2015-08-19       Impact factor: 2.457

6.  A Robust Protocol for Pd(II)-catalyzed C-3 Arylation of (1H) Indazoles and Pyrazoles: Total Synthesis of Nigellidine Hydrobromide.

Authors:  Mengchun Ye; Andrew J F Edmunds; James A Morris; David Sale; Yejia Zhang; Jin-Quan Yu
Journal:  Chem Sci       Date:  2013-06-01       Impact factor: 9.825

Review 7.  Developing ligands for palladium(II)-catalyzed C-H functionalization: intimate dialogue between ligand and substrate.

Authors:  Keary M Engle; Jin-Quan Yu
Journal:  J Org Chem       Date:  2013-05-03       Impact factor: 4.354

8.  Pd(II)-Catalyzed C3-Selective Arylation of Pyridine with (Hetero)arenes.

Authors:  Guo-Lin Gao; Wujiong Xia; Pankaj Jain; Jin-Quan Yu
Journal:  Org Lett       Date:  2016-02-02       Impact factor: 6.005

9.  Organoborohydride-catalyzed Chichibabin-type C4-position alkylation of pyridines with alkenes assisted by organoboranes.

Authors:  Ying Wang; Runhan Li; Wei Guan; Yanfei Li; Xiaohong Li; Jianjun Yin; Ge Zhang; Qian Zhang; Tao Xiong; Qian Zhang
Journal:  Chem Sci       Date:  2020-09-29       Impact factor: 9.825

10.  Regioselective reactions of 3,4-pyridynes enabled by the aryne distortion model.

Authors:  Adam E Goetz; Neil K Garg
Journal:  Nat Chem       Date:  2012-11-25       Impact factor: 24.427
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.