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Issue 46, 2017
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Efficient cross-coupling of aryl/alkenyl triflates with acyclic secondary alkylboronic acids

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Abstract

Aryl–secondary alkyl cross-coupling with aryl sulfonate esters as coupling partners remains a significant challenge. Efficient cross-coupling between aryl/alkenyl triflates and acyclic secondary alkylboronic acids is realized for the first time to provide a series of sterically congested acyclic secondary alkyl arenes/olefins in good to excellent yields. The employment of sterically bulky P,P[double bond, length as m-dash]O ligand L1/L2 is crucial for the high yields and selectivities. The method has enabled a concise and 4-step synthesis of a key intermediate of male contraceptive agent and PAF antagonist gossypol.

Graphical abstract: Efficient cross-coupling of aryl/alkenyl triflates with acyclic secondary alkylboronic acids

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Publication details

The article was received on 12 Oct 2017, accepted on 10 Nov 2017 and first published on 13 Nov 2017


Article type: Paper
DOI: 10.1039/C7OB02531A
Citation: Org. Biomol. Chem., 2017,15, 9903-9909
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    Efficient cross-coupling of aryl/alkenyl triflates with acyclic secondary alkylboronic acids

    T. Si, B. Li, W. Xiong, B. Xu and W. Tang, Org. Biomol. Chem., 2017, 15, 9903
    DOI: 10.1039/C7OB02531A

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