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首页> 外文期刊>Chemistry: A European journal >Boron Lewis Acid-Catalyzed Hydroboration of Alkenes with Pinacolborane: BAr3F Does What B(C6F5)(3) Cannot Do
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Boron Lewis Acid-Catalyzed Hydroboration of Alkenes with Pinacolborane: BAr3F Does What B(C6F5)(3) Cannot Do

机译：频那醇硼烷在路易斯路易斯酸催化的烯烃加氢硼化中：BAr3F做B（C6F5）（3）无法做的事情

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摘要

The transition-metal-free hydroboration of various alkenes with pinacolborane (HBpin) initiated by tris[3,5-bis(trifluoromethyl) phenyl] borane (BArF3) is reported. The choice of the boron Lewis acid is crucial as the more prominent boron Lewis acid tris(pentafluorophenyl)borane (B(C6F5)(3)) is reluctant to react. Unlike B(C6F5)(3), BAr3F is found to engage in substituent redistribution with HBpin, resulting in the formation of ArFBpin and the electron- deficient diboranes [H2BArF] 2 and [(ArF)(H) B(mH) 2BAr(2)(F)]. These in situ-generated hydroboranes undergo regioselective hydroboration of styrene derivatives as well as aliphatic alkenes with cis diastereoselectivity. Another ligand metathesis of these adducts with HBpin subsequently affords the corresponding HBpin-derived anti-Markovnikov adducts. The reactive hydroboranes are regenerated in this step, thereby closing the catalytic cycle.
机译：报道了由三[3,5-双（三氟甲基）苯基]硼烷（BArF3）引发的频哪醇硼烷（HBpin）对各种烯烃的无过渡金属氢硼化。硼路易斯酸的选择至关重要，因为更重要的硼路易斯酸三（五氟苯基）硼烷（B（C6F5）（3））不愿反应。与B（C6F5）（3）不同，发现BAr3F与HBpin一起参与取代基的重新分布，导致形成ArFBpin和缺电子的乙硼烷[H2BArF] 2和[（ArF）（H）B（mH）2BAr（ 2）（F）]。这些原位生成的氢硼烷经历了顺式非对映选择性的苯乙烯衍生物以及脂族烯烃的区域选择性氢硼化。这些加合物与HBpin的另一种配体复分解随后提供了相应的HBpin衍生的抗Markovnikov加合物。反应性氢硼烷在该步骤中再生，从而关闭催化循环。

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