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CBr 作为卤键供体催化剂,用于选择性活化苯甲醛合成α,β-不饱和酮。

CBr as a Halogen Bond Donor Catalyst for the Selective Activation of Benzaldehydes to Synthesize α,β-Unsaturated Ketones.

机构信息

Department of Chemistry, Indian Institute of Technology Madras , Chennai, 600036, India.

出版信息

Org Lett. 2017 Mar 3;19(5):1244-1247. doi: 10.1021/acs.orglett.7b00348. Epub 2017 Feb 17.

DOI:10.1021/acs.orglett.7b00348
PMID:28212043
Abstract

CBr has been employed as a halogen bond donor catalyst for the selective activation of aldehyde, to achieve an efficient solvent- and metal-free C═C bond forming reaction in the presence of strong acid sensitive groups such as methoxy, cyanide, ester, and ketal for the synthesis of α,β-unsaturated ketones. This unique capability of CBr to act as a halogen bond donor has been explored and established using UV-vis as well as IR spectroscopy. Moreover, this unprecedented methodology enables the synthesis of the pharmaceutically important molecule licochalcone A.

摘要

CBr 已被用作卤键供体催化剂,用于选择性活化醛,在存在强酸性敏感基团如甲氧基、氰基、酯和缩酮的情况下,实现有效的溶剂和无金属 C═C 键形成反应,用于合成α,β-不饱和酮。使用 UV-vis 和 IR 光谱探索并建立了 CBr 作为卤键供体的这种独特能力。此外,这种前所未有的方法学能够合成具有重要药用价值的分子甘草查尔酮 A。

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