Ipso Nitration of Aryl Boronic Acids Using Fuming Nitric Acid

被引：19

作者：

Murray, James, I ^{[1
]}

Elipe, Maria V. Silva ^{[2
]}

Baucom, Kyle D. ^{[1
]}

Brown, Derek B. ^{[1
]}

Quasdorf, Kyle ^{[1
]}

Caille, Seb ^{[1
]}

机构：

[1] Amgen Inc, Proc Dev, Pivotal & Commercial Synthet, Drug Subst Technol, Thousand Oaks, CA 91320 USA

[2] Amgen Inc, Attribute Sci, Thousand Oaks, CA 91320 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 04期

关键词：

ARYLBORONIC ACIDS; AROMATIC NITRATION; CARBOXYLIC-ACIDS; EFFICIENT; HALIDES; HALOGENATION; METHODOLOGY; KINETICS; CATALYST; ORDER;

D O I：

10.1021/acs.joc.1c00886

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The ipso nitration of aryl boronic acid derivatives has been developed using fuming nitric acid as the nitrating agent. This facile procedure provides efficient and chemoselective access to a variety of aromatic nitro compounds. While several activating agents and nitro sources have been reported in the literature for this synthetically useful transformation, this report demonstrates that these processes likely generate a common active reagent, anhydrous HNO3. Kinetic and mechanistic studies have revealed that the reaction order in HNO3 is >2 and indicate that the (NO2)-N-center dot radical is the active species.

引用

页码：1977 / 1985

页数：9

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