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Issue 42, 2017
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Pd-Catalysed Suzuki coupling of α-bromoethenylphosphonates with organotrifluoroborates: a general protocol for the synthesis of terminal α-substituted vinylphosphonates

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Abstract

A general and robust protocol for the synthesis of terminal α-substituted vinylphosphonates via Suzuki coupling of α-bromovinylphosphonates with organotrifluoroborates has been successfully developed. This method features a broad substrate scope, great functional group compatibilities, and easy scale-up ability. In addition to easy access of nucleophiles, a straightforward synthesis of electrophiles was also realized with diethyl α-bromoethenylphosphonate as the starting material. With a combination of Pd2(dba)3/SPhos as the catalyst, a range of α-alkyl, aryl, heteroaryl, and alkynyl substituted ethenylphosphonates could be nicely accessed under mild conditions. As a synthetic application, the terminal vinylphosphonate was utilized as an effective Michael acceptor in the visible-light-promoted Giese reaction.

Graphical abstract: Pd-Catalysed Suzuki coupling of α-bromoethenylphosphonates with organotrifluoroborates: a general protocol for the synthesis of terminal α-substituted vinylphosphonates

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Publication details

The article was received on 10 Sep 2017, accepted on 09 Oct 2017 and first published on 09 Oct 2017


Article type: Paper
DOI: 10.1039/C7OB02267K
Citation: Org. Biomol. Chem., 2017,15, 8985-8989
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    Pd-Catalysed Suzuki coupling of α-bromoethenylphosphonates with organotrifluoroborates: a general protocol for the synthesis of terminal α-substituted vinylphosphonates

    L. Zhang, Y. Fang, X. Jin, H. Xu, R. Li, H. Wu, B. Chen, Y. Zhu, Y. Yang and Z. Tian, Org. Biomol. Chem., 2017, 15, 8985
    DOI: 10.1039/C7OB02267K

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