TY - JOUR
T1 - Alkyne Trifunctionalization via Divergent Gold Catalysis
T2 - Combining π-Acid Activation, Vinyl-Gold Addition, and Redox Catalysis
AU - Yuan, Teng
AU - Tang, Qi
AU - Shan, Chuan
AU - Ye, Xiaohan
AU - Wang, Jin
AU - Zhao, Pengyi
AU - Wojtas, Lukasz
AU - Hadler, Nicholas
AU - Chen, Hao
AU - Shi, Xiaodong
N1 - Publisher Copyright:
© 2021 American Chemical Society.
PY - 2021/3/17
Y1 - 2021/3/17
N2 - 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).
AB - 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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U2 - 10.1021/jacs.1c01811
DO - 10.1021/jacs.1c01811
M3 - Article
C2 - 33661619
AN - SCOPUS:85103227314
SN - 0002-7863
VL - 143
SP - 4074
EP - 4082
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 10
ER -