Identifying the Roles of Amino Acids, Alcohols and 1,2-Diamines as Mediators in Coupling of Haloarenes to Arenes

被引：123

作者：

Zhou, Shengze ^{[1
]}

Doni, Eswararao ^{[1
]}

Anderson, Greg M. ^{[1
]}

Kane, Ryan G. ^{[1
]}

MacDougall, Scott W. ^{[1
]}

Ironmonger, Victoria M. ^{[2
]}

Tuttle, Tell ^{[1
]}

Murphy, John A. ^{[1
]}

机构：

[1] Univ Strathclyde, Dept Pure & Appl Chem, WestCHEM, Glasgow G1 1XL, Lanark, Scotland

[2] GlaxoSmithletne Med Res Ctr, Stevenage SG1 2NY, Herts, England

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2014年 / 136卷 / 51期

基金：

英国工程与自然科学研究理事会;

关键词：

C-H-ARYLATION; POTASSIUM TERT-BUTOXIDE; SUPER-ELECTRON-DONORS; UNSOLVATED MAGNESIUM DIISOPROPYLAMIDE; METAL-FREE SYNTHESIS; UNACTIVATED ARENES; NUCLEOPHILIC TRIFLUOROMETHYLATION; ARYL BROMIDES; INTRAMOLECULAR ARYLATION; ORGANIC-SYNTHESIS;

D O I：

10.1021/ja5101036

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Coupling of haloarenes to arenes has been facilitated by a diverse range of organic additives in the presence of KOtBu or NaOtBu since the first report in 2008. Very recently, we showed that the reactivity of some of these additives (e.g., compounds 6 and 7) could be explained by the formation of organic electron donors in situ, but the role of other additives was not addressed. The simplest of these, alcohols, including 1,2-diols, 1,2-diamines, and amino acids are the most intriguing, and we now report experiments that support their roles as precursors of organic electron donors, underlining the importance of this mode of initiation in these coupling reactions.

引用

页码：17818 / 17826

页数：9

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