Pd(OH)2/C, a Practical and Efficient Catalyst for the Carboxylation of Benzylic Bromides with Carbon Monoxide,Organic Process Research & Development

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Pd(OH)2/C, a Practical and Efficient Catalyst for the Carboxylation of Benzylic Bromides with Carbon Monoxide
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2019-12-19 , DOI: 10.1021/acs.oprd.9b00402
Anne-Marie Wakuluk-Machado ₁ , Damien F. Dewez ₁ , Hajar Baguia ₁ , Miguel Imbratta ₂ , Pierre-Georges Echeverria ₂ , Gwilherm Evano ₁

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A simple, efficient, cheap, and broadly applicable system for the carboxylation of benzylic bromides with carbon monoxide and water is reported. Upon simple reaction with only 2.5 wt % of Pearlman’s catalyst and 10 mol % of tetrabutylammonium bromide in tetrahydrofuran at 110 °C for 4 h, a range of benzylic bromides can be smoothly converted to the corresponding arylacetic acids in good to excellent yields after simple extraction and acid–base wash. The reaction was found to be broadly applicable, scalable, and could be successfully extended to the use of ex situ-generated carbon monoxide and applied to the synthesis of the nonsteroidal anti-inflammatory drug diclofenac.

中文翻译：

Pd（OH）₂ / C，一种实用高效的一氧化碳对苄基溴化物进行羧化的催化剂

报道了一种简单，有效，便宜且广泛适用的系统，用于用一氧化碳和水羧化苄基溴。在110°C下仅与2.5 wt％的Pearlman's催化剂和10 mol％的四丁基溴化铵在四氢呋喃中简单反应4小时，即可将一系列苄基溴平稳地转化为相应的芳酸，简单萃取后收率良好。和酸碱洗涤。该反应被发现具有广泛的适用性，可扩展性，并且可以成功地扩展到非原位产生的一氧化碳的使用，并可以应用于非甾体类抗炎药双氯芬酸的合成。

更新日期：2019-12-19

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