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Pd-Senphos Catalyzed trans-Selective Cyanoboration of 1,3-Enynes.
Angew Chem Int Ed Engl. 2020 09 07; 59(37):15928-15932.AC

Abstract

The first trans-selective cyanoboration reaction of an alkyne, specifically a 1,3-enyne, is described. The reported palladium-catalyzed cyanoboration of 1,3-enynes is site-, regio-, and diastereoselective, and is uniquely enabled by the 1,4-azaborine-based Senphos ligand structure. Tetra-substituted alkenyl nitriles are obtained providing useful boron-dienenitrile building blocks that can be further functionalized. The utility of our method has been demonstrated with the synthesis of Satigrel, an anti-platelet aggregating agent.

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Authors+Show Affiliations

Zhang Y
Department of Chemistry, Boston College, Chestnut Hill, MA, 02467-3860, USA.
Li B
Department of Chemistry, Boston College, Chestnut Hill, MA, 02467-3860, USA.
Liu SY
Department of Chemistry, Boston College, Chestnut Hill, MA, 02467-3860, USA.

MeSH

BoranesCatalysisCyanidesDensity Functional TheoryFatty Acids, MonounsaturatedHydrocarbonsPalladiumPlatelet Aggregation InhibitorsStereoisomerism

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural

Language

eng

PubMed ID

32511855

Citation

Zhang, Yuanzhe, et al. "Pd-Senphos Catalyzed trans-Selective Cyanoboration of 1,3-Enynes." Angewandte Chemie (International Ed. in English), vol. 59, no. 37, 2020, pp. 15928-15932.
Zhang Y, Li B, Liu SY. Pd-Senphos Catalyzed trans-Selective Cyanoboration of 1,3-Enynes. Angew Chem Int Ed Engl. 2020;59(37):15928-15932.
Zhang, Y., Li, B., & Liu, S. Y. (2020). Pd-Senphos Catalyzed trans-Selective Cyanoboration of 1,3-Enynes. Angewandte Chemie (International Ed. in English), 59(37), 15928-15932. https://doi.org/10.1002/anie.202005882
Zhang Y, Li B, Liu SY. Pd-Senphos Catalyzed trans-Selective Cyanoboration of 1,3-Enynes. Angew Chem Int Ed Engl. 2020 09 7;59(37):15928-15932. PubMed PMID: 32511855.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Pd-Senphos Catalyzed trans-Selective Cyanoboration of 1,3-Enynes. AU - Zhang,Yuanzhe, AU - Li,Bo, AU - Liu,Shih-Yuan, Y1 - 2020/07/16/ PY - 2020/04/23/received PY - 2020/6/9/pubmed PY - 2021/3/30/medline PY - 2020/6/9/entrez KW - azaborine KW - enyne KW - palladium KW - trans-cyanoboration SP - 15928 EP - 15932 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 59 IS - 37 N2 - The first trans-selective cyanoboration reaction of an alkyne, specifically a 1,3-enyne, is described. The reported palladium-catalyzed cyanoboration of 1,3-enynes is site-, regio-, and diastereoselective, and is uniquely enabled by the 1,4-azaborine-based Senphos ligand structure. Tetra-substituted alkenyl nitriles are obtained providing useful boron-dienenitrile building blocks that can be further functionalized. The utility of our method has been demonstrated with the synthesis of Satigrel, an anti-platelet aggregating agent. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/32511855/Pd_Senphos_Catalyzed_trans_Selective_Cyanoboration_of_13_Enynes_ DB - PRIME DP - Unbound Medicine ER -