Amino‐λ3‐iodane‐Enabled Electrophilic Amination of Arylboronic Acid Derivatives

Author:

Kiyokawa Kensuke1ORCID,Kawanaka Kazuki1,Minakata Satoshi1ORCID

Affiliation:

1. Department of Applied Chemistry Graduate School of Engineering Osaka University Yamadaoka 2-1 Suita Osaka 565-0871 Japan

Abstract

AbstractIn this report, we describe the use of amino‐λ3‐iodanes in the electrophilic amination of arylboronic acids and boronates. Iodine(III) reagents with transferable amino groups, including one with an NH2 group, were synthesized and used in the amination, allowing the synthesis of a wide range of primary and secondary (hetero)arylamines. Mechanistic studies by DFT calculations indicate that the reaction proceeds through an electrophilic amination process from a tetravalent borate complex with a B−N dative bond.

Funder

Japan Society for the Promotion of Science

Japan Science and Technology Agency

Asahi Glass Foundation

Uehara Memorial Foundation

Publisher

Wiley

Reference75 articles.

1. S. A. Lawrence Ed.:Amines: Synthesis Properties and Applications; Cambridge University Press: Cambridge 2004.

2. S. Caron A. Ghosh Nucleophilic Aromatic Substitution. InPractical Synthetic Organic Chemistry: Reactions Principles and Techniques; Wiley: Hoboken NJ USA 2011; pp 237–253.

3. G. A. Olah M. Ripudaman S. C. Narang Nitration: Methods and Mechanisms; VCH Publishers Inc.: New York 1989.

4.  

5. Evolution of a Fourth Generation Catalyst for the Amination and Thioetherification of Aryl Halides

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