Synthesis and stability study of isocyano aryl boronate esters and their synthetic applications

doi:10.1039/C5RA27624A

機構典藏 > College of Sciences > Graduate Institute & Department of Chemistry > Journal Article > Item 987654321/112969

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Title:	Synthesis and stability study of isocyano aryl boronate esters and their synthetic applications
Authors:	Fang, Hao-Ping;Fu, Chia-Chieh;Tai, Chin-Kuen;Chang, Ken-Hao;Yang, Ru-Han;Wu, Meng-Ju;Chen, Hsien-Chi;Li, Chia-Jung;Huang, Shi-Qing;Lien, Wan-Hsiang
Date:	2016-03-17
Issue Date:	2018-03-15 12:10:57 (UTC+8)
Abstract:	A facile synthesis of isocyano arylboronate esters is reported. Although tri-coordinate boron functional groups are commonly recognized as vulnerable to nucleophilic attack, the newly reported tri-coordinate isocyano arylboronate esters were found to be stable, albeit owing to the presence of an isocyano group. Theoretical calculations, using the DFT/B3LYP/6-31G(d,p) method, revealed that the electron delocalization between the aryl group and the boron atom might contribute to this stability. UV-vis spectroscopic investigations on 2-(4-isocyanophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2a) were in agreement with the theoretical studies, showing a red-shifted absorption compared with that of phenylisonitrile. The reported strategy allows boronate ester substrates to survive throughout two-step operations. Two of the compounds synthesized were successfully exploited in Ugi and Passerini multicomponent reactions to afford corresponding products. In addition, two boron-containing tetrazoles were also prepared under environmentally benign conditions. These results demonstrated that functionalized isocyanides are stable and can be used as strategically as synthetic building blocks.
Relation:	RSC Advances 6(36), p.30362-30371
DOI:	10.1039/C5RA27624A
Appears in Collections:	[Graduate Institute & Department of Chemistry] Journal Article

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