使用 O-(二苯基膦酰基)羟胺 (DPPH) 对芳基硼酸和酯进行快速和一般胺化处理

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-11-14 DOI:10.1021/acs.orglett.4c03625

Matthew G. Kung, Polpum Onnuch, Richard Y. Liu

{"title":"使用 O-(二苯基膦酰基)羟胺 (DPPH) 对芳基硼酸和酯进行快速和一般胺化处理","authors":"Matthew G. Kung, Polpum Onnuch, Richard Y. Liu","doi":"10.1021/acs.orglett.4c03625","DOIUrl":null,"url":null,"abstract":"O-(Diphenylphosphinyl)hydroxylamine (DPPH) is a general reagent for the conversion of (hetero)aryl boronic acids and esters to primary anilines. The transformation proceeds rapidly at rt and exhibits a broad substrate scope and exceptional functional-group tolerance. In terms of rate, the reaction is relatively insensitive to the electronic properties of the substrate, in contrast to similar reactions using electrophilic amination reagents such as hydroxylamine-O-sulfonic acid. Consequently, this protocol is particularly useful for accessing electron-deficient (hetero)aryl anilines, which had been challenging to prepare using prior methods.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9000,"publicationDate":"2024-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Rapid and General Amination of Aryl Boronic Acids and Esters Using O-(Diphenylphosphinyl)hydroxylamine (DPPH)\",\"authors\":\"Matthew G. Kung, Polpum Onnuch, Richard Y. Liu\",\"doi\":\"10.1021/acs.orglett.4c03625\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"O-(Diphenylphosphinyl)hydroxylamine (DPPH) is a general reagent for the conversion of (hetero)aryl boronic acids and esters to primary anilines. The transformation proceeds rapidly at rt and exhibits a broad substrate scope and exceptional functional-group tolerance. In terms of rate, the reaction is relatively insensitive to the electronic properties of the substrate, in contrast to similar reactions using electrophilic amination reagents such as hydroxylamine-O-sulfonic acid. Consequently, this protocol is particularly useful for accessing electron-deficient (hetero)aryl anilines, which had been challenging to prepare using prior methods.\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":4.9000,\"publicationDate\":\"2024-11-14\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1021/acs.orglett.4c03625\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.4c03625","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}

引用次数: 0

摘要

O-(二苯基膦酰)羟胺（DPPH）是一种将（杂）芳基硼酸和酯转化为伯胺的通用试剂。该转化反应在恒温条件下快速进行，具有广泛的底物范围和优异的官能团耐受性。就速率而言，该反应对底物的电子特性相对不敏感，这与使用亲电氨基化试剂（如羟胺-O-磺酸）的类似反应截然不同。因此，这种方法特别适用于获得缺电子的（杂）芳基苯胺，而用以前的方法制备这类苯胺具有挑战性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Rapid and General Amination of Aryl Boronic Acids and Esters Using O-(Diphenylphosphinyl)hydroxylamine (DPPH)

查看原文本刊更多论文

Rapid and General Amination of Aryl Boronic Acids and Esters Using O-(Diphenylphosphinyl)hydroxylamine (DPPH)

O-(Diphenylphosphinyl)hydroxylamine (DPPH) is a general reagent for the conversion of (hetero)aryl boronic acids and esters to primary anilines. The transformation proceeds rapidly at rt and exhibits a broad substrate scope and exceptional functional-group tolerance. In terms of rate, the reaction is relatively insensitive to the electronic properties of the substrate, in contrast to similar reactions using electrophilic amination reagents such as hydroxylamine-O-sulfonic acid. Consequently, this protocol is particularly useful for accessing electron-deficient (hetero)aryl anilines, which had been challenging to prepare using prior methods.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.