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Divergent Protosilylation and Protoborylation of Polar Enynes

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journal contribution
posted on 02.04.2019 by Fei-Fan Meng, Qi-Yan Xue, Bing Jiang, Meng Zhao, Jia-Hao Xie, Yun-He Xu, Teck-Peng Loh
Copper-catalyzed divergent conjugate protosilylation and protoborylation of polar enynes were developed. The corresponding β-boryldienoates and β-silyldienotes were obtained in moderate to good yields and with good stereoselectivity. In this protocol, novel cascade double protoborylation/protodeboronation processes of polar enynoates enabled access of the useful trisubstituted vinylboronates in up to 80% yield and with up to 98:2 Z/E ratio. Moreover, divergent transformations of the products thus obtained were also investigated.

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