An Efficient and Recyclable Catalytic System Comprising Nano-Iridium(0) and a Pyridinium Salt of nido-Carboranyldiphosphine for the Synthesis of One-Dimensional Boronate Esters via Hydroboratio

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• 作者：Yinghuai Zhu ; Shi Hui Agnes Jang ; Yue Hao Tham ; Oh Biying Algin ; John A. Maguire ; Narayan S. Hosmane
• 刊名：Organometallics
• 出版年：2012
• 出版时间：April 9, 2012
• 年：2012
• 卷：31
• 期：7
• 页码：2589-2596
• 全文大小：996K
• 年卷期：v.31,no.7(April 9, 2012)
• ISSN：1520-6041

文摘

The reaction of N-pentyl-4-methylpyridinium bromide with Na[7,8-bis(dicyclohexylphosphino)-7,8-dicarba-nido-C₂B₉H₁₀] led to the formation of a pyridinium salt of the carboranyldiphosphine ligand, [N-pentyl-4-methylpyridinium]⁺[7,8-bis(dicyclohexylphosphino)-7,8-dicarba-nido-C₂B₉H₁₀]^{鈭?/sup> (1), in 86% yield. [7,8-bis(dicyclohexylphosphino)-7,8-dicarba-nido-C₂B₉H₁₀]鈭?/sup> was produced in situ from the decapitation of 1,2-bis(dicyclohexylphosphino)-1,2-dicarba-closo-dodecaborane with sodium hydroxide. Ligand 1 is highly soluble in ionic liquids such as trihexyltetradecylphosphonium dodecylbenzene sulfonate ([THTdP][DBS]) and 1-hexyl-3-methylimidazolium trifluoromethansulfonate ([HMIM][CF₃SO₃]) and was used as a bulky catalyst composite with the ionic liquids [THTdP][DBS] and [HMIM][CF₃SO₃], with stabilized iridium(0) nanoparticles produced by thermolysis of Ir₄(CO)₁₂, or with the iridium complex [Ir(coe)₂Cl]₂ (coe = cyclooctene) and in the ionic liquid [THTdP][DBS] and [HMIM][CF₃SO₃] for the hydroboration of methyl oleate (MO), methyl 10-undecenoate, and 1-hexene. The new Ir(0) catalytic system was found to be efficient, robust, and recyclable so that a number of repetitious hydroborations of MO with high product selectivity could be accomplished.}