{"title":"控制羧酸区域选择性安装以合成 2,3-二芳基丙酸的方法学","authors":"Mason Hamilton, Trina M. Perrone, Brian Popp","doi":"10.1002/adsc.202400952","DOIUrl":null,"url":null,"abstract":"A stepwise copper-catalyzed boracarboxylation then palladium-catalyzed Suzuki-Miyaura cross-coupling methodology was developed to access 2,3-diarylpropionic acid derivatives regioselectively by pre-setting the position of the carboxylic acid in the boracarboxylation reaction. This method provides access to a wide range of aryl and heteroaryl products in up to 80% isolated yield. Pharmaceutical potential was demonstrated by synthesizing a glucagon receptor antagonist drug in 3-steps (31% overall yield) from commercially available 4-tert-butylstyrene.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"108 1","pages":""},"PeriodicalIF":4.4000,"publicationDate":"2024-10-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Methodology to Control the Regioselective Installation of a Carboxylic Acid for the Synthesis of 2,3-Diarylpropionic Acids\",\"authors\":\"Mason Hamilton, Trina M. Perrone, Brian Popp\",\"doi\":\"10.1002/adsc.202400952\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"A stepwise copper-catalyzed boracarboxylation then palladium-catalyzed Suzuki-Miyaura cross-coupling methodology was developed to access 2,3-diarylpropionic acid derivatives regioselectively by pre-setting the position of the carboxylic acid in the boracarboxylation reaction. This method provides access to a wide range of aryl and heteroaryl products in up to 80% isolated yield. Pharmaceutical potential was demonstrated by synthesizing a glucagon receptor antagonist drug in 3-steps (31% overall yield) from commercially available 4-tert-butylstyrene.\",\"PeriodicalId\":118,\"journal\":{\"name\":\"Advanced Synthesis & Catalysis\",\"volume\":\"108 1\",\"pages\":\"\"},\"PeriodicalIF\":4.4000,\"publicationDate\":\"2024-10-10\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Advanced Synthesis & Catalysis\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1002/adsc.202400952\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, APPLIED\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Advanced Synthesis & Catalysis","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/adsc.202400952","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}
Methodology to Control the Regioselective Installation of a Carboxylic Acid for the Synthesis of 2,3-Diarylpropionic Acids
A stepwise copper-catalyzed boracarboxylation then palladium-catalyzed Suzuki-Miyaura cross-coupling methodology was developed to access 2,3-diarylpropionic acid derivatives regioselectively by pre-setting the position of the carboxylic acid in the boracarboxylation reaction. This method provides access to a wide range of aryl and heteroaryl products in up to 80% isolated yield. Pharmaceutical potential was demonstrated by synthesizing a glucagon receptor antagonist drug in 3-steps (31% overall yield) from commercially available 4-tert-butylstyrene.
期刊介绍：
Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry.
The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.
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