Alkyne Trifunctionalization via Divergent Gold Catalysis: Combining π-Acid Activation, Vinyl-Gold Addition, and Redox Catalysis
Document Type
Article
Publication Date
3-17-2021
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).
Identifier
85103227314 (Scopus)
Publication Title
Journal of the American Chemical Society
External Full Text Location
https://doi.org/10.1021/jacs.1c01811
e-ISSN
15205126
ISSN
00027863
PubMed ID
33661619
First Page
4074
Last Page
4082
Issue
10
Volume
143
Grant
CHE-1665122
Fund Ref
National Science Foundation
Recommended Citation
Yuan, Teng; Tang, Qi; Shan, Chuan; Ye, Xiaohan; Wang, Jin; Zhao, Pengyi; Wojtas, Lukasz; Hadler, Nicholas; Chen, Hao; and Shi, Xiaodong, "Alkyne Trifunctionalization via Divergent Gold Catalysis: Combining π-Acid Activation, Vinyl-Gold Addition, and Redox Catalysis" (2021). Faculty Publications. 4242.
https://digitalcommons.njit.edu/fac_pubs/4242