Key Laboratory of Organic Optoelectronics & Molecular Engineering of Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 100084, China.
State Key Laboratory of Chemistry and Utilization of Carbon-Based Energy Resources, College of Chemistry, Xinjiang University, Urumqi 830017, China.
J Org Chem. 2022 Dec 2;87(23):16011-16018. doi: 10.1021/acs.joc.2c02150. Epub 2022 Nov 15.
Benzo[]fluorenes were synthesized via CuI-catalyzed cascade reactions of 2-alkynylbenzaldehyde -tosylhydrazones and aromatic terminal alkynes in the presence of base including the formation of the benzoenyne-allene intermediate and its Schmittel cyclization. Density functional theory calculation was performed to give the energy difference for the formation of 5-phenyl-11-benzo[]fluorene and 1,2-diphenyl-1-cyclobuta[]indene from the proposed diradical intermediates.
苯并[]芴类化合物是通过 CuI 催化的 2-炔基苯甲醛-对甲苯磺酰腙和芳基末端炔烃的级联反应在碱的存在下合成的，包括苯乙炔-丙二烯中间体的形成和其施密特环化反应。进行了密度泛函理论计算，以给出从所提出的自由基中间体形成 5-苯基-11-苯并[]芴和 1,2-二苯基-1-环丁[]茚的能量差。
