通过钯催化四取代 -二氟烯烃的 C-F 键活化构建手性二氟 1,3-二烯的立体选择性合成。
Stereoselective Synthesis of Difluorinated 1,3-Dienes via Palladium-Catalyzed C-F Bond Activation of Tetrasubstituted -Difluoroalkenes.
机构信息
Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, China.
出版信息
Org Lett. 2021 Jul 2;23(13):5241-5245. doi: 10.1021/acs.orglett.1c01768. Epub 2021 Jun 11.
A highly diastereoselective Pd(0)-catalyzed synthesis of difluorinated 1,3-dienes is described. Symmetrical 1,3-dienes containing a vicinal difluoro moiety can be obtained as single diastereomers from tetrasubstituted -difluoroalkenes. The reaction presumably proceeds through a stereoselective twofold Pd-catalyzed Miyaura borylation/Suzuki-Miyaura cross-coupling of the C-F bond. Moreover, modular synthesis of unsymmetrical difluorinated 1,3-dienes is also achievable by the coupling between -difluoroalkenes and borylated monofluoroalkenes.
本文描述了一种高度非对映选择性的 Pd(0)催化合成二氟代 1,3-二烯的方法。含有顺式二氟基团的对称 1,3-二烯可以从四取代的-difluoroalkenes 中作为单一非对映异构体获得。该反应可能通过立体选择性的 Pd 催化两次 Miyaura 硼酸化/Suzuki-Miyaura 交叉偶联 C-F 键进行。此外，通过-difluoroalkenes 和硼酸化单氟代烯烃的偶联也可以实现不对称二氟代 1,3-二烯的模块化合成。
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