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首页> 外文期刊>Chemistry: A European journal >Fe-Catalyzed One-Pot Oxidative Cleavage of Unsaturated Fatty Acids into Aldehydes with Hydrogen Peroxide and Sodium Periodate
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Fe-Catalyzed One-Pot Oxidative Cleavage of Unsaturated Fatty Acids into Aldehydes with Hydrogen Peroxide and Sodium Periodate

机译：铁在过氧化氢和高碘酸钠的催化下将不饱和脂肪酸一锅氧化裂解为醛

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摘要

A one-pot method has been developed for the oxidative cleavage of internal alkenes into aldehydes by using 0.5 mol % of the nonheme iron complex [Fe(OTf)_2(mix-bpbp)] (bpbp = N,N'-bis(2-picolyl)-2,2'-bipyrrolidine) as catalyst and 1.5 equivalents of hydrogen peroxide and 1 equivalent of sodium periodate as oxidants. A mixture of diastereomers of the chiral bpbp ligand can be used, thereby omitting the need for resolution of its optically active components. The cleavage reaction can be performed in one pot within 20 h and under ambient conditions. Addition of water after the epoxidation, acidification and subsequent pH neutralization are crucial to perform the epoxidation, hydrolysis, and subsequent diol cleavage in one pot. High aldehyde yields can be obtained for the cleavage of internal aliphatic double bonds with cis and trans configuration (86-98%) and unsaturated fatty acids and esters (69-96%). Good aldehyde yields are obtained in reactions of trisubstituted and terminal alkenes (62-63%). The products can be easily isolated by a simple extraction step with an organic solvent. The presented protocol involves a lower catalyst loading than conventional methods based on Ru or Os. Also, hydrogen peroxide can be used as the oxidant in this case, which is often disproportionated by second- and third-row metals. By using only mild oxidants, overoxidation of the aldehyde to the carboxylic acid is prevented.
机译：通过使用0.5摩尔％的非血红素铁络合物[Fe（OTf）_2（mix-bpbp）]（bpbp = N，N'-bis（2），已开发出一种一锅法将内部烯烃氧化裂解为醛（-picolyl）-2,2'-bipyrrolidine）作为催化剂，使用1.5当量的过氧化氢和1当量的高碘酸钠作为氧化剂。可以使用手性bpbp配体的非对映异构体的混合物，从而不需要拆分其旋光组分。裂解反应可以在20小时内在环境条件下在一个罐中进行。环氧化，酸化和随后的pH中和后加水对于在一锅中进行环氧化，水解和随后的二醇裂解至关重要。对于具有顺式和反式构型的内脂族双键（86-98％）和不饱和脂肪酸和酯（69-6％）的裂解，可以获得较高的醛收率。在三取代和末端烯烃的反应中，醛的收率很高（62-63％）。可以通过简单的有机溶剂萃取步骤轻松分离出产物。提出的协议涉及比基于Ru或Os的常规方法更低的催化剂负载量。同样，在这种情况下，过氧化氢可以用作氧化剂，通常被第二行和第三行金属所歧化。通过仅使用温和的氧化剂，可以防止醛过度氧化为羧酸。

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