Tracking the Process of a Solvothermal Domino Reaction Leading to a Stable Triheteroarylmethyl Radical: A Combined Crystallographic and Mass-Spectrometric Study.
作者信息
Liu Bin, Yu Fei, Tu Min, Zhu Zhong-Hong, Zhang Yuexing, Ouyang Zhong-Wen, Wang Zhenxing, Zeng Ming-Hua
机构信息
Hubei Collaborative Innovation Center for Advanced Organic Chemical Materials, Ministry of Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules, College of Chemistry and Chemical Engineering, Hubei University, Wuhan, 430062, P. R. China.
Department Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences Guangxi Normal University, Guilin, 541004, P. R. China.
出版信息
Angew Chem Int Ed Engl. 2019 Mar 18;58(12):3748-3753. doi: 10.1002/anie.201813829. Epub 2019 Jan 21.
A new free carbon radical was obtained in a microwave-assisted solvothermal reaction of the primary amine (1-methyl-1H-benzo[d]imidazol-2-yl)methanamine with FeCl ⋅6 H O in methanol at 140 °C. Through a combination of crystallography and electrospray ionization mass spectrometry, the reaction process was studied. The longest domino reaction includes 14 steps and forms up to 12 new covalent bonds (9 C-N and 3 C-C bonds) and 3 five-membered heterocycles. For the first time, the homolytic cleavage of a C-O bond was used to synthesize a triarylmethyl radical.
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