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 - Funding Information:
We are grateful to the NSF (CHE-1665122) and NIH (1R01GM120240-01) for financial support. This work has been supported in part by University of South Florida Interdisciplinary NMR Facility and the Chemical Purification, Analysis, and Screening (CPAS) Core Facility, The Department of Chemistry and the College of Arts and Sciences, Tampa, Florida. Dedicated to the 100 anniversary of Chemistry at Nankai University. th
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).
UR - http://www.scopus.com/inward/record.url?scp=85103227314&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85103227314&partnerID=8YFLogxK
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 -