Copper-Mediated Conversion of Complex Ethers to Esters: Enabling Biopolymer Depolymerisation under Mild Conditions.,Chemistry - A European Journal

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Copper-Mediated Conversion of Complex Ethers to Esters: Enabling Biopolymer Depolymerisation under Mild Conditions.
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2020-05-07 , DOI: 10.1002/chem.202000088
Ganyuan Xiao ₁ , James R D Montgomery ₁ , Christopher S Lancefield ₁ , Isabella Panovic ₁ , Nicholas J Westwood ₁

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Selective processing of the β‐O‐4 unit in lignin is essential for the efficient depolymerisation of this biopolymer and therefore its successful integration into a biorefinery set‐up. An approach is described in which this unit is modified to incorporate a carboxylic ester with the goal of enabling the use of mild depolymerisation conditions. Inspired by preliminary results using a Cu/TEMPO/O₂ system, a protocol was developed that gave the desired β‐O‐4‐containing ester in high yield using certain dimeric model compounds. The optimised reaction conditions were then applied to an oligomeric lignin model system. Extensive 2D NMR analysis demonstrated that analogous chemistry could be achieved with the oligomeric substrate. Mild depolymerisation of the ester‐containing oligomer delivered the expected aryl acid monomer.

中文翻译：

铜介导的复杂醚向酯的转化：在温和条件下实现生物聚合物解聚。

木质素中β- O -4 单元的选择性加工对于这种生物聚合物的有效解聚至关重要，因此能够成功整合到生物精炼装置中。描述了一种方法，其中对该单元进行修改以掺入羧酸酯，目的是能够使用温和的解聚条件。受 Cu/TEMPO/O ₂系统初步结果的启发，开发了一种方案，使用某些二聚模型化合物以高产率提供所需的含β- O -4 的酯。然后将优化的反应条件应用于低聚木质素模型系统。广泛的 2D NMR 分析表明，可以使用低聚底物实现类似的化学反应。含酯低聚物的温和解聚产生了预期的芳基酸单体。

更新日期：2020-05-07

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