Remote ether groups-directed regioselective and chemoselective cycloaddition of azides and alkynes |
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Institution: | State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Department of Pharmaceutical Science, Dalian University of Technology, Dalian 116024, China |
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Abstract: | Remote ether groups could be used as directing groups to prepare fully substituted 5-ether-1,2,3-triazoles with exclusive 1,5-regioselectivities and excellent chemoselectivities. Ether group could coordinate with iridium catalyst by lone-pair electron at a distance (up to four σ bonds) away from alkyne to control the regioselectivity by weak coordination effect. The cycloaddition reaction chemoselectively occurred at the propargyl ether moiety of diyne to give unique fully substituted 4-alkynyl-triazole. |
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