Alkyne Trifunctionalization via Divergent Gold Catalysis: Combining π‑Acid Activation, Vinyl–Gold Addition, and Redox Catalysis
journal contributionposted on 04.03.2021, 20:10 by Teng Yuan, Qi Tang, Chuan Shan, Xiaohan Ye, Jin Wang, Pengyi Zhao, Lukasz Wojtas, Nicholas Hadler, Hao Chen, Xiaodong Shi
Here we report the first example of alkyne trifunctionalization through simultaneous construction of C–C, C–O, and C–N bonds via gold catalysis. With the assistance of a γ-keto directing group, sequential gold-catalyzed alkyne hydration, vinyl–gold nucleophilic addition, and gold(III) reductive elimination were achieved in one pot. Diazonium salts were identified as both electrophiles (N source) and oxidants (C source). Vinyl–gold(III) intermediates were revealed as effective nucleophiles toward diazonium, facilitating nucleophilic addition and reductive elimination with high efficiency. The rather comprehensive reaction sequence was achieved with excellent yields (up to 95%) and broad scope (>50 examples) under mild conditions (room temperature or 40 °C).
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sequential gold-catalyzed alkyne hy...Divergent Gold CatalysisDiazonium saltsreductive eliminationnucleophilic additiondiazoniumActivationreaction sequenceassistanceN sourceconstructionγ- ketoelectrophileRedox Catalysisyieldalkyne trifunctionalizationintermediateoxidantscopenucleophileAlkyne TrifunctionalizationC sourceefficiencygold catalysisroom temperaturebond