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Rhodium(I)-Catalyzed Defluorinative Coupling of Boronic Acids with Monofluoroalkenes
Organic Letters ( IF 4.9 ) Pub Date : 2022-08-04 , DOI: 10.1021/acs.orglett.2c02294 Yuwei Zong 1 , Yihan Tang 1 , Gavin Chit Tsui 1
Organic Letters ( IF 4.9 ) Pub Date : 2022-08-04 , DOI: 10.1021/acs.orglett.2c02294 Yuwei Zong 1 , Yihan Tang 1 , Gavin Chit Tsui 1
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We herein describe a highly selective Rh(I)-catalyzed defluorinative coupling of boronic acids with (E)-β-monofluoroacrylates. In contrast to previous methods, the trisubstituted (Z)-alkene products were obtained in excellent dr with an inversion of double bond geometry. Experimental and computational studies established that Rh(I)-facilitated β-F elimination is favored over competing β-H elimination and protodemetalation.
中文翻译:
铑 (I) 催化硼酸与单氟烯烃的脱氟偶联
我们在此描述了硼酸与 ( E )-β-单氟丙烯酸酯的高选择性 Rh(I) 催化的脱氟偶联。与以前的方法相比,三取代的 ( Z )-烯烃产物以优异的 dr 获得,双键几何形状反转。实验和计算研究表明,Rh(I) 促进的 β-F 消除优于竞争性 β-H 消除和原脱金属。
更新日期:2022-08-04
中文翻译:
铑 (I) 催化硼酸与单氟烯烃的脱氟偶联
我们在此描述了硼酸与 ( E )-β-单氟丙烯酸酯的高选择性 Rh(I) 催化的脱氟偶联。与以前的方法相比,三取代的 ( Z )-烯烃产物以优异的 dr 获得,双键几何形状反转。实验和计算研究表明,Rh(I) 促进的 β-F 消除优于竞争性 β-H 消除和原脱金属。