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Palladium-catalyzed NHC ligand-controlled regiodivergent allyl-fluoroallyl cross-couplings
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2024-11-21 , DOI: 10.1039/d4qo01800a Yangyang Ma, Boxia Xu, Hua Zhang, Zhiping Li
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2024-11-21 , DOI: 10.1039/d4qo01800a Yangyang Ma, Boxia Xu, Hua Zhang, Zhiping Li
The palladium-catalyzed cross-coupling of (E)-2-fluoroallyl carbonates and allylboronates is reported. The regioselectivity is susceptive to the steric requirements of the NHC ligand, with small IMes favoring linear fluorinated 1,5-dienes, while IPrBIDEA featuring sterically-congested character benefits branched products. Control experiments revealed that either 2-fluoroallyl carbonates or gem-F2CPs could undergo allylation with excellent regioselectivity, yet the former showed somewhat lower branched reactivity.
中文翻译:
钯催化的 NHC 配体控制的区域发散烯丙基-氟烯丙基交叉偶联
报道了 (E)-2-氟烯丙基碳酸酯和烯丙基硼酸盐的钯催化交叉偶联。区域选择性容易受到 NHC 配体的空间位阻要求的影响,小 IMe 有利于线性氟化 1,5-二烯,而具有空间充塞特性的 IPrBIDEA 有利于支链产物。对照实验表明,2-氟烯丙基碳酸酯或 gem-F 2CPs 可以以优异的区域选择性进行烯丙基化,但前者显示出略低的支链反应性。
更新日期:2024-11-21
中文翻译:
钯催化的 NHC 配体控制的区域发散烯丙基-氟烯丙基交叉偶联
报道了 (E)-2-氟烯丙基碳酸酯和烯丙基硼酸盐的钯催化交叉偶联。区域选择性容易受到 NHC 配体的空间位阻要求的影响,小 IMe 有利于线性氟化 1,5-二烯,而具有空间充塞特性的 IPrBIDEA 有利于支链产物。对照实验表明,2-氟烯丙基碳酸酯或 gem-F 2CPs 可以以优异的区域选择性进行烯丙基化,但前者显示出略低的支链反应性。