Reshaping aromatic frameworks: expansion of aromatic system drives metallabenzenoids to metallapentalenes

Li, Qian1; Fei, Jiawei1; Ruan, Kaidong1; Hua, Yuhui2; Chen, Dafa2; Luo, Ming2; Xia, Haiping1,2

2023-04-01

10.1039/d3sc01491f

CHEMICAL SCIENCE   影响因子和分区

2041-6520

2041-6539

Reshaping an aromatic framework to generate other skeletons is a challenging issue due to the stabilization energy of aromaticity. Such reconfigurations of aromatics commonly generate non-aromatic products and hardly ever reshape to a different aromatic framework. Herein, we present the transformation of metallaindenols to metallapentalenes and metallaindenes in divergent pathways, converting one aromatic framework to another with an extension of the conjugation framework. The mechanistic study of this transformation shows that phosphorus ligands play different roles in the divergent processes. Further theoretical studies indicate that the expansion of the aromatic system is the driving force promoting this skeletal rearrangement. Our findings offer a new concept and strategy to reshape and construct aromatic compounds.

SCI ; EI

英语

NI论文

通讯

Natural Science Foundation of China["21931002","22071098","92156021","22101115"] ; Shenzhen Science and Technology Innovation Committee["JCYJ20200109140812302","JCYJ20210324105013035"] ; Guangdong Provincial Key Laboratory of Catalysis[2020B121201002] ; Introduction of Major Talent Projects in Guangdong Province[2019CX01C079]

Chemistry

Chemistry, Multidisciplinary

WOS:000983128900001

ROYAL SOC CHEMISTRY

20232014098915

Aromatic compounds ; Aromatization

Chemical Reactions:802.2 ; Organic Compounds:804.1 ; Materials Science:951

Web of Science

1.Xiamen Univ, Coll Chem & Chem Engn, State Key Lab Phys Chem Solid Surfaces, Xiamen 361005, Peoples R China
2.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Dept Chem, Shenzhen 518055, Peoples R China

Li, Qian,Fei, Jiawei,Ruan, Kaidong,et al. Reshaping aromatic frameworks: expansion of aromatic system drives metallabenzenoids to metallapentalenes[J]. CHEMICAL SCIENCE,2023,14(21):5672-5680.

Li, Qian.,Fei, Jiawei.,Ruan, Kaidong.,Hua, Yuhui.,Chen, Dafa.,...&Xia, Haiping.(2023).Reshaping aromatic frameworks: expansion of aromatic system drives metallabenzenoids to metallapentalenes.CHEMICAL SCIENCE,14(21),5672-5680.

Li, Qian,et al."Reshaping aromatic frameworks: expansion of aromatic system drives metallabenzenoids to metallapentalenes".CHEMICAL SCIENCE 14.21(2023):5672-5680.