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Photoredox-catalyzed branch-selective pyridylation of alkenes for the expedient synthesis of Triprolidine.
Nat Commun 2019; 10(1):749NC

Abstract

Alkenylpyridines are important pharmaceutical cores as well as versatile building blocks in organic synthesis. Heck reaction represents one of the most powerful platform for the construction of aryl-substituted alkenes, nevertheless, examples for Heck type coupling of alkenes with pyridines, particularly with branched selectivity, remain elusive. Here we report a catalytic, branch-selective pyridylation of alkenes via a sulfinate assisted photoredox catalysis. This reaction proceeds through a sequential radical addition/coupling/elimination, by utilizing readily available sodium sulfinates as reusable radical precursors as well as traceless elimination groups. This versatile protocol allows for the installation of important vinylpyridines with complete branched selectivity under mild conditions. Furthermore, this catalytic manifold is successfully applied to the expedient synthesis of Triprolidine.

Authors+Show Affiliations

State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, Center for Advanced Low-Dimension Materials, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, 201620, Shanghai, China.State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, Center for Advanced Low-Dimension Materials, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, 201620, Shanghai, China.State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, Center for Advanced Low-Dimension Materials, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, 201620, Shanghai, China.State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, Center for Advanced Low-Dimension Materials, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, 201620, Shanghai, China.State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, Center for Advanced Low-Dimension Materials, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, 201620, Shanghai, China. lingling.chu1@dhu.edu.cn.

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

30765695

Citation

Zhu, Shengqing, et al. "Photoredox-catalyzed Branch-selective Pyridylation of Alkenes for the Expedient Synthesis of Triprolidine." Nature Communications, vol. 10, no. 1, 2019, p. 749.
Zhu S, Qin J, Wang F, et al. Photoredox-catalyzed branch-selective pyridylation of alkenes for the expedient synthesis of Triprolidine. Nat Commun. 2019;10(1):749.
Zhu, S., Qin, J., Wang, F., Li, H., & Chu, L. (2019). Photoredox-catalyzed branch-selective pyridylation of alkenes for the expedient synthesis of Triprolidine. Nature Communications, 10(1), p. 749. doi:10.1038/s41467-019-08669-1.
Zhu S, et al. Photoredox-catalyzed Branch-selective Pyridylation of Alkenes for the Expedient Synthesis of Triprolidine. Nat Commun. 2019 02 14;10(1):749. PubMed PMID: 30765695.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Photoredox-catalyzed branch-selective pyridylation of alkenes for the expedient synthesis of Triprolidine. AU - Zhu,Shengqing, AU - Qin,Jian, AU - Wang,Fang, AU - Li,Huan, AU - Chu,Lingling, Y1 - 2019/02/14/ PY - 2018/10/07/received PY - 2019/01/23/accepted PY - 2019/2/16/entrez PY - 2019/2/16/pubmed PY - 2019/2/16/medline SP - 749 EP - 749 JF - Nature communications JO - Nat Commun VL - 10 IS - 1 N2 - Alkenylpyridines are important pharmaceutical cores as well as versatile building blocks in organic synthesis. Heck reaction represents one of the most powerful platform for the construction of aryl-substituted alkenes, nevertheless, examples for Heck type coupling of alkenes with pyridines, particularly with branched selectivity, remain elusive. Here we report a catalytic, branch-selective pyridylation of alkenes via a sulfinate assisted photoredox catalysis. This reaction proceeds through a sequential radical addition/coupling/elimination, by utilizing readily available sodium sulfinates as reusable radical precursors as well as traceless elimination groups. This versatile protocol allows for the installation of important vinylpyridines with complete branched selectivity under mild conditions. Furthermore, this catalytic manifold is successfully applied to the expedient synthesis of Triprolidine. SN - 2041-1723 UR - https://www.unboundmedicine.com/medline/citation/30765695/Photoredox-catalyzed_branch-selective_pyridylation_of_alkenes_for_the_expedient_synthesis_of_Triprolidine L2 - http://dx.doi.org/10.1038/s41467-019-08669-1 DB - PRIME DP - Unbound Medicine ER -