4-甲基噻吩衍生物与HBr/HO的可见光诱导C(sp)-H溴化反应
Visible-light-induced C(sp)-H bromination of 4-methylthiophene derivatives with HBr/HO.
作者信息
Song Wenbo, Ma Ming, Zhang Wenjing, Feng Ranran, Lu Congcong, Zhang Hong-Yu, Zhang Yuecheng, Zhao Jiquan
机构信息
School of Chemical Engineering and Technology, Hebei University of Technology, Tianjin 300131, China.
Hebei Provincial Key Laboratory of Green Chemical Technology and High Efficient Energy Saving, Tianjin 300131, China.
出版信息
Org Biomol Chem. 2024 May 22;22(20):4145-4152. doi: 10.1039/d4ob00547c.
A convenient method to synthesize ethyl 4-(bromomethyl)thiophene-3-carboxylate derivatives has been developed a visible-light-induced radical process in good yields and with wide functional group tolerance under air conditions and at ambient temperature. The present protocol has the advantages of a high atom economy, easy purification, and environmental friendliness as it employs HBr as the bromine source and the cheap and low-toxic HO as the oxidant. The synthetic utility of this method is demonstrated by a gram scale reaction and its application in the innovative synthesis of the clinical drug relugolix.
已开发出一种合成4-(溴甲基)噻吩-3-羧酸乙酯衍生物的简便方法，该方法是在空气条件和室温下通过可见光诱导的自由基过程，产率良好且具有广泛的官能团耐受性。本方法具有原子经济性高、易于纯化和环境友好等优点，因为它使用HBr作为溴源，廉价且低毒的HO作为氧化剂。该方法的合成实用性通过克级反应及其在临床药物relugolix创新合成中的应用得到了证明。
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