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Selective and efficient synthesis of trans-arylvinylboronates and trans-hetarylvinylboronates using palladium catalyzed cross-coupling

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Abstract

trans-Arylvinylboronate derivatives are important synthesis blocks in natural products, pharmaceuticals and organic materials. There are only a few reaction conditions that could selectively provide trans-arylvinylboronates by Heck coupling of pinacol vinylboronate and aryl halides. Here we report an efficient and versatile method of palladium catalyzed cross-coupling between pinacol vinylboronate and various aryl or hetaryl bromides to obtain the corresponding trans-(het)arylvinylboronates in excellent yields and selectivity. 30 examples have been synthesized using this protocol which offers an alternative method to prepare these useful building blocks.

Graphical abstract: Selective and efficient synthesis of trans-arylvinylboronates and trans-hetarylvinylboronates using palladium catalyzed cross-coupling

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Publication details

The article was received on 19 Dec 2016, accepted on 16 Mar 2017, published on 17 Mar 2017 and first published online on 17 Mar 2017


Article type: Paper
DOI: 10.1039/C6NJ03984G
Citation: New J. Chem., 2017, Advance Article
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    Selective and efficient synthesis of trans-arylvinylboronates and trans-hetarylvinylboronates using palladium catalyzed cross-coupling

    Z. Liu, W. Wei, L. Xiong, Q. Feng, Y. Shi, N. Wang and L. Yu, New J. Chem., 2017, Advance Article , DOI: 10.1039/C6NJ03984G

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