Synthesis of 2-Hydroxymethyl Ketones by Ruthenium Hydride-Catalyzed Cross-Coupling Reaction of α,β-Unsaturated Aldehydes with Primary Alcohols
Synthesis of 2-Hydroxymethyl Ketones by Ruthenium Hydride-Catalyzed Cross-Coupling Reaction of α,β-Unsaturated Aldehydes with Primary Alcohols
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DOI：
10.1021/ol902289r
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发表时间：
2010-01-01
期刊：
影响因子：
5.2
通讯作者：
Ryu, Ilhyong
中科院分区：
文献类型：
--
作者：
Denichoux, Aurelien;Fukuyama, Takahide;Ryu, Ilhyong
在RuHCl（CO）（PPh 3）（3）催化下，α，β-不饱和醛与伯醇发生交叉偶联反应生成2-羟甲基酮。这种原子经济性反应可能通过α，β-不饱和醛的氢化钌化，然后所得烯醇化物与醛的羟醛缩合反应得到α-甲酰化酮，其与伯醇进行转移氢化，得到α-羟甲基酮。还原步骤可以产生醛，参与下一个催化循环。
The cross-coupling reaction of alpha,beta-unsaturated aldehydes with primary alcohols to give 2-hydroxymethyl ketones was achieved using RuHCl(CO)(PPh3)(3) as a catalyst. This atom-economical reaction is likely to proceed via the hydroruthenation of alpha,beta-unsaturated aldehydes followed by an aldol reaction of the resultant enolates with aldehydes to give alpha-formylated ketones, which undergo transfer hydrogenation with primary alcohols leading to a-hydroxymethyl ketones. The reduction step can generate aldehydes, participating In the next catalytic cycle.