多氯甲基化和卤化螺[5,5]三烯酮的合成——联芳基炔酮的去芳构化螺环化。
Synthesis of polychloromethylated and halogenated spiro[5,5]trienones dearomative spirocyclization of biaryl ynones.
机构信息
Guangling College and School of Plant Protection, Yangzhou University, Yangzhou 225009, P. R. China.
Anhui Laboratory of Clean Catalytic Engineering, Anhui Laboratory of Functional Complexes for Materials Chemistry and Application, College of Chemical and Environmental Engineering, Anhui Polytechnic University, Wuhu, Anhui 241000, P. R. China.
出版信息
Org Biomol Chem. 2022 Aug 24;20(33):6659-6666. doi: 10.1039/d2ob01053d.
We disclosed a selective polychloromethylation and halogenation reaction of alkynes a radical addition/spirocyclization cascade sequence, in which polyhaloalkanes were used as the precursor for polyhalomethyl and halogen radicals. Using this strategy, a series of valuable halogen-, CHCl- or CCl-containing spiro[5,5]trienones were synthesized in good yields with good functional group tolerance in one pot under simple and mild conditions. It is noted that an unprecedented halogenation instead of dibromomethylation was achieved when CHBr was used in this work.
我们揭示了炔烃的一种选择性多氯甲基化和卤化反应——自由基加成/螺环化级联序列，其中多卤代烷用作多卤甲基和卤代自由基的前体。利用该策略，在简单温和的条件下一锅法以良好的收率和良好的官能团耐受性合成了一系列有价值的含卤素、CHCl 或 CCl 的螺[5.5]三烯酮。值得注意的是，当在这项工作中使用 CHBr 时，实现了前所未有的卤化而不是二溴甲基化。
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