Cross-coupling of 2-methylquinolines and in-situ activated isoquinolines: Construction of 1,2-disubstituted isoquinolinones

• Published in: Chinese chemical letters 2022-11, Vol.33 (11), p.4874-4877
• Main Authors: Shi, Jianyi, Zeng, Zheng, Xu, Shengting, Cai, Zechun, Luo, Yuehua, Fan, Yongbo, Zhu, Zhongzhi, Wen, Tingting, Chen, Xiuwen
• Format: Article
• Language: English
• Subjects: In-situ activated; Isoquinolinones; One-pot; Three-component reaction; Trifunctionalisation
• ISSN: 1001-8417; 1878-5964
• DOI: 10.1016/j.cclet.2022.02.032

In this study, a method was developed to form C(sp3)–C(sp2) bonds via copper catalyst-promoted cross coupling of 2-methylquinoline and in-situ-activated 3-haloisoquinoline under mild conditions. The multi-component tandem reaction was used to construct new C–N, C=O and C–C bonds in one pot via sequential functionalization of the N1, C3 and C1 positions of 3-haloisoquinoline. This method can be used to efficiently access 1,2-disubstituted isoquinolinones by the three-component reaction of 3-halogen isoquinoline, alkyl halide, and 2-methylquinoline. Herein, a method was developed to form C(sp3)-C(sp2) bonds through a copper catalyst-promoted cross coupling of 2-methylquinoline and in-situ activated 3-haloisoquinoline under mild conditions. The multi-component tandem reaction constructed new C-N, C=O, and C-C bonds in one pot through the sequential functionalization of the N1, C3, and C1 positions of 3-haloisoquinoline. This method can efficiently construct 1,2-disubstituted isoquinolinones through the three-component reaction of 3-halogen isoquinoline, alkyl halide, and 2-methylquinoline. [Display omitted]