Wu Junliang, Deng Xiaozhou, Yoshikai Naohiko
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore, 637371, Singapore.
College of Chemistry and Molecular Engineering, Henan Institutes of Advanced Technology, Zhengzhou University, Zhengzhou, 450001, P.R. China.
Chemistry. 2019 Jun 12;25(33):7839-7842. doi: 10.1002/chem.201901543. Epub 2019 May 13.
We report herein the synthesis of highly substituted and stereochemically well-defined vinylbenziodoxole (VBX) derivatives through hydrochlorination and iodochlorination of ethynylbenziodoxoles. The hydrochlorination is achieved using pyridine hydrochloride as an HCl source in an anti-fashion under mild, open-air conditions to afford a 2-chlorinated VBX product, which serves as a useful building block for the stereoselective synthesis of trisubstituted alkenes. Meanwhile, iodochlorination with iodine monochloride proceeds in an unusual syn-pathway, stereoselectively affording a tetrasubstituted VBX derivative.
我们在此报告通过乙炔基苯碘酰化合物的氢氯化和碘氯化反应合成高度取代且立体化学明确的乙烯基苯碘酰（VBX）衍生物。氢氯化反应是在温和的露天条件下，以反式方式使用盐酸吡啶作为HCl源实现的，得到一种2-氯化的VBX产物，它是立体选择性合成三取代烯烃的有用构建块。同时，用一氯化碘进行的碘氯化反应以不寻常的顺式途径进行，立体选择性地得到一种四取代的VBX衍生物。
