Efficient boron-copper additions to aryl-substituted alkenes promoted by NHC-based catalysts. enantioselective Cu-catalyzed hydroboration reactions.
Efficient boron-copper additions to aryl-substituted alkenes promoted by NHC-based catalysts. enantioselective Cu-catalyzed hydroboration reactions.
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DOI：
10.1021/ja809382c
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发表时间：
2009-03-11
影响因子：
15
通讯作者：
Hoveyda AH
中科院分区：
文献类型：
--
作者：
Lee Y;Hoveyda AH
报道了一种铜催化的无环和环状二取代芳基烯烃硼铜加成反应的方法。用0.5-5摩尔%的容易获得的N-杂环卡宾（NHC）络合物促进反应; MeOH的存在促进C-Cu键的原位质子化并导致有效的催化剂周转，构成净Cu催化的硼氢化过程。反应以>98：<2的位点选择性进行，并提供补充通过硼氢化物试剂的反应或通过Rh-或Ir-催化的硼氢化（苄基仲C-B键）获得的那些的仲有机硼烷异构体。公开了关于由手性NHC络合物催化的过程的初步观察，以高达99：1的对映体比例递送产物。
A Cu-catalyzed method for efficient boron-copper addition processes involving acyclic and cyclic disubstituted aryl olefins are reported. Reactions are promoted with 0.5–5 mol % of a readily available N-heterocyclic carbene (NHC) complex; the presence of MeOH promotes in situ protonation of the C–Cu bond and leads to efficient catalyst turnover, constituting a net Cu-catalyzed hydroboration process. Reactions proceed in >98:<2 site-selectivity, and furnish secondary organoborane isomers that complement those obtained through reactions of boron-hydride reagents or by Rh- or Ir-catalyzed hydroborations (benzylic secondary C–B bonds). Initial observations regarding processes catalyzed by chiral NHC complexes, delivering products in up to 99:1 enantiomeric ratio, are disclosed.
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影响因子：
16.6
作者：
Brown, M. Kevin;May, Tricia L.;Hoveyda, Amir H.
通讯作者：
Hoveyda, Amir H.
影响因子：
2.8
作者：
Lillo, Vanesa;Prieto, Auxiliadora;Fernandez, Elena
通讯作者：
Fernandez, Elena
影响因子：
2.8
作者：
Laitar, David S.;Tsui, Emily Y.;Sadighi, Joseph P.
通讯作者：
Sadighi, Joseph P.
影响因子：
15
作者：
Chaulagain, Mani Raj;Sormunen, Grant J.;Montgomery, John
通讯作者：
Montgomery, John
影响因子：
2.8
作者：
Dang, Li;Lin, Zhenyang;Marder, Todd B.
通讯作者：
Marder, Todd B.