Teng Yuan1, Qi Tang1, Chuan Shan1, Xiaohan Ye1, Jin Wang2, Pengyi Zhao3, Lukasz Wojtas1, Nicholas Hadler1, Hao Chen3, Xiaodong Shi1. 1. Department of Chemistry, University of South Florida, Tampa, Florida 33620, United States. 2. College of Chemistry, Chemical Engineering and Material Science, Shandong Normal University, Jinan, Shandong 250014, China. 3. Department of Chemistry and Environmental Science, New Jersey Institute of Technology, Newark, New Jersey 07102, United States.
Abstract
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).
Here we report the first example of alkyne trifunctionalization through simultaneous construction of C-C, C-O, and C-n class="Chemical">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).