Synthesis of Boron-Containing Primary Amines

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Title:	Synthesis of Boron-Containing Primary Amines
Authors:	Chung, Sheng-Hsuan;Lin, Ting-Ju;Hu, Qian-Yu;Tsai, Chia-Hua;Pan, Po-Shen
Contributors:	淡江大學化學學系
Keywords:	boron;multicomponent reactions;Gabriel synthesis;Ugi reaction;peptoid
Date:	2013-10
Issue Date:	2013-10-22 16:38:42 (UTC+8)
Publisher:	Basel: M D P I AG
Abstract:	In this study, boron-containing primary amines were synthesized for use as building blocks in the study of peptoids. In the first step, Gabriel synthesis conditions were modified to enable the construction of seven different aminomethylphenyl boronate esters in good to excellent yields. These compounds were further utilized to build peptoid analogs via an Ugi four-component reaction (Ugi-4CR) under microwave irradiation. The prepared Ugi-4CR boronate esters were then successfully converted to the corresponding boronic acids. Finally, the peptoid structures were successfully modified by cross-coupling to aryl/heteroaryl chlorides via a palladium-mediated Suzuki coupling reaction to yield the corresponding derivatives in moderate to good yields.
Relation:	Molecules 18(10), pp.12346-12367
DOI:	10.3390/molecules181012346
Appears in Collections:	[Graduate Institute & Department of Chemistry] Journal Article

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