Metal‐Free Direct Transformation of Aryl Boronic Acid to Primary Amines

In this work, we report a transition‐metal free approach for the construction of primary aromatic amines from aryl boronic acids and esters with N‐Boc‐O‐tosylhydroxylamine as an amine surrogate. Bench stable TsONHBoc is easy to use and it produces a non‐interfering water‐soluble by‐product. The prot...

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Bibliographic Details
Published inEuropean journal of organic chemistry Vol. 2022; no. 27
Main Authors Kumar, Puneet, Verma, Saumya, Rathi, Komal, Chandra, Dinesh, Prakash Verma, Ved, Jat, Jawahar L.
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 21.07.2022
Subjects
Amines
Aromatic compounds
Boronic acid
Boronic ester
Esters
Metal-free amination
N-Boc-O-tosylhydroxylamine
Primary aromatic amine
Substrates
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Summary:In this work, we report a transition‐metal free approach for the construction of primary aromatic amines from aryl boronic acids and esters with N‐Boc‐O‐tosylhydroxylamine as an amine surrogate. Bench stable TsONHBoc is easy to use and it produces a non‐interfering water‐soluble by‐product. The protocol is operative for both electron‐rich and electron‐deficient aryl boronic acids under acidic conditions, where the former arenes affords a better yield of the desired product. Even, sterically hindered and halogenated substrates are easily amenable under this reaction condition. The current protocol can be scaled up to produce gram‐scale primary aromatic amines. In this work a transition‐metal free primary amination of aryl boronic acids and esters has been developed by using bench stable N‐Boc‐O‐tosylhydroxylamine as the nitrogen donor. This method has several advantages, such as operational simplicity, air tolerance, scalability, water soluble by‐products, good to high yields, and good functional group tolerance.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202200508