N-Heterocyclic Carbene Promoted Decarboxylation of Lignin-Derived Aromatic Acids,ACS Sustainable Chemistry & Engineering

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N-Heterocyclic Carbene Promoted Decarboxylation of Lignin-Derived Aromatic Acids
ACS Sustainable Chemistry & Engineering ( IF 7.1 ) Pub Date : 2018-04-16 00:00:00 , DOI: 10.1021/acssuschemeng.7b03612
Dajiang Liu _{1,

2} , Jian Sun _{1,

2} , Blake A. Simmons _{1,

3} , Seema Singh _{1,

2,

4}

Affiliation

Decarboxylation is an important reaction in organic synthesis and drug discovery, which is typically catalyzed by strong bases or metal-based catalysts bearing low yield and selectivity. For the first time, we demonstrated a new strategy of decarboxylation of hydroxyl cinnamic acids such as p-coumaric acid, ferulic acid, sinapinic acid, and caffeic acid in the presence of N-heterocyclic carbene (NHC) precursors (i.e., 1-ethyl-3-methyl imidazolium acetate [C₂C₁Im][OAc]), achieving high yields and selectivities up to 100% under relatively mild conditions. [C₂C₁Im][OAc] showed excellent recyclability as organocatalysis during three times of recycling using biphasic reaction system. A mechanistic study revealed that the decarboxylation was catalyzed by NHCs that were in-situ generated by self-deprotonation of [C₂C₁Im][OAc]. Our demonstrated route is especially appealing for the production of lignin-derived renewable aromatics.

中文翻译：

N-杂环碳烯促进木质素衍生的芳酸脱羧

脱羧作用是有机合成和药物开发中的重要反应，通常由具有低收率和选择性的强碱或金属基催化剂催化。我们首次展示了在N-杂环卡宾（NHC）前体（即1-乙基）存在下对羟基肉桂酸（例如对香豆酸，阿魏酸，芥子酸和咖啡酸）进行脱羧的新策略。-3-甲基乙酸咪唑鎓盐[C ₂ C ₁ Im] [OAc]），在相对温和的条件下可获得高收率和高达100％的选择性。[C ₂ C ₁Im] [OAc]在使用双相反应系统进行的三次循环中表现出优异的可循环性，作为有机催化剂。机理研究表明，脱羧作用是由[C ₂ C ₁ Im] [OAc]的自我去质子化所产生的NHC催化的。我们证明的路线特别适合生产木质素衍生的可再生芳烃。

更新日期：2018-04-16

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