Iron porphyrin-catalysed C(sp(3))-H amination with alkyl azides for the synthesis of complex nitrogen-containing compounds

Fan, Jianqiang1; Wang, Ye1; Hu, Xuefu1; Liu, Yungen1; Che, Chi-Ming1,2,3,4

2023-02-01

10.1039/d2qo01972h

Organic Chemistry Frontiers   Impact Factor & Quartile

2052-4129

Transition metal-catalysed direct C-N bond formation via nitrenoid (metal-imido/nitrene complexes) insertion, such as C-H bond amination, is a powerful strategy for preparing nitrogen-containing organic compounds. In this context, metal catalysts based on iron are appealing due to iron's high Earth abundance and biocompatibility. Herein, we demonstrate that iron(iii) NHC porphyrin-catalysed C(sp(3))-H amination with alkyl azides, using [Fe-III(TDCPP)(IMe)(2)]I (H2TDCPP = tetrakis(2,6-dichlorophenyl)porphyrin, IMe = 1,3-dimethylimidazol-2-ylidene) as a catalyst, offers a complementary approach for the synthesis of structurally complex organic compounds as exemplified by the synthesis of a panel of nitrogen-containing skeletons that are representative examples of various families of natural products and bioactive compounds.

SCI

English

First ; Corresponding

Shenzhen Science and Technology Innovation Commission[17304019] ; General Research Fund from the Hong Kong Research Grants Council["21871127","91856203"] ; null[JCYJ20190809141203613] ; null[17301817]

Chemistry

Chemistry, Organic

WOS:000928682700001

ROYAL SOC CHEMISTRY

Web of Science

1.Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Guangdong, Peoples R China
2.Univ Hong Kong, Dept Chem, State Key Lab Synthet Chem, Pokfulam Rd, Hong Kong, Peoples R China
3.HKU Shenzhen Inst Res & Innovat, Shenzhen 518057, Guangdong, Peoples R China
4.Lab Synthet Chem & Chem Biol Ltd, Units 1503 1511, 15-F,Bldg 17W,Hong Kong Sci Pk, Hong Kong, Peoples R China

Fan, Jianqiang,Wang, Ye,Hu, Xuefu,et al. Iron porphyrin-catalysed C(sp(3))-H amination with alkyl azides for the synthesis of complex nitrogen-containing compounds[J]. Organic Chemistry Frontiers,2023.

Fan, Jianqiang,Wang, Ye,Hu, Xuefu,Liu, Yungen,&Che, Chi-Ming.(2023).Iron porphyrin-catalysed C(sp(3))-H amination with alkyl azides for the synthesis of complex nitrogen-containing compounds.Organic Chemistry Frontiers.

Fan, Jianqiang,et al."Iron porphyrin-catalysed C(sp(3))-H amination with alkyl azides for the synthesis of complex nitrogen-containing compounds".Organic Chemistry Frontiers (2023).