Stereocontrolled Synthesis of Halovinylbenziodoxoles by Hydro- and Iodochlorination of Ethynylbenziodoxoles |
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Authors: | Prof Dr Junliang Wu Xiaozhou Deng Prof Naohiko Yoshikai |
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Institution: | Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore, 637371 Singapore |
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Abstract: | 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. |
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Keywords: | alkynes cross-coupling dihalogenation hydrohalogenation hypervalent iodine compounds |
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