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Synthesis of Boron-Containing Primary Amines
Department of Chemistry, Tamkang University, No. 151 Yingzhuan rd., Tamsui Dist., New Taipei City 25137, Taiwan
* Author to whom correspondence should be addressed.
Received: 30 August 2013; in revised form: 27 September 2013 / Accepted: 30 September 2013 / Published: 8 October 2013
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.
Keywords: boron; multicomponent reactions; Gabriel synthesis; Ugi reaction; peptoid
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Chung, S.-H.; Lin, T.-J.; Hu, Q.-Y.; Tsai, C.-H.; Pan, P.-S. Synthesis of Boron-Containing Primary Amines. Molecules 2013, 18, 12346-12367.
Chung S-H, Lin T-J, Hu Q-Y, Tsai C-H, Pan P-S. Synthesis of Boron-Containing Primary Amines. Molecules. 2013; 18(10):12346-12367.
Chung, Sheng-Hsuan; Lin, Ting-Ju; Hu, Qian-Yu; Tsai, Chia-Hua; Pan, Po-Shen. 2013. "Synthesis of Boron-Containing Primary Amines." Molecules 18, no. 10: 12346-12367.