A modified Click-style Sonogashira coupling reaction has been developed which can deprotect silyl-protected aromatic alkynes and couple aromatic iodides through trimethylsilyl acetylene and bistrimethylsilyl acetylene at room temperature. Good yields are possible, the transformation is tolerant of electron-deficient and –rich aryl halide systems, and minimum homocoupling products are observed. The transformation protocol involves Pd(dba)2 catalyst, sodium ascorbate, copper (II) sulfate, and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as the base. The solvent system makes use of an acetonitrile/water mixture and it is likely the combination of the water and Cu2+ which allows for in situ silyl protecting group removal and consequent Sonogashira coupling.

Click-style Sonogashira deprotection and coupling reactions involving silyl-protected alkynes at room temperature

2019 Spring National Meeting

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