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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Published in | European journal of organic chemistry Vol. 2022; no. 27 |
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Main Authors | , , , , , |
Format | Journal Article |
Language | English |
Published |
Weinheim
Wiley Subscription Services, Inc
21.07.2022
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Subjects | |
Online Access | Get full text |
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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. |
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ISSN: | 1434-193X 1099-0690 |
DOI: | 10.1002/ejoc.202200508 |