TY - JOUR
T1 - Two Distinct Gold-Catalyzed Oxidative Annulations of 1,5-Allenynes with Nitrones to Yield 1-Naphthol Derivatives Bearing 2,3- versus 3,4-Fused Nitroxy Rings
AU - Barik, Debashis
AU - Maitra, Chandrima
AU - Hsieh, Chi Tien
AU - Cheng, Mu Jeng
AU - Liu, Rai Shung
N1 - Publisher Copyright:
© 2024 American Chemical Society.
PY - 2024/2/2
Y1 - 2024/2/2
N2 - Gold-catalyzed nitrone oxidations of 1,5-allenynes are postulated to involve the formation of gold-enolate containing all carbon 1,3-dipole-like species Int-4, further yielding 1-naphthols fused with a nitroxy ring. 1,5-Allenynes bearing internal alkynes (R = aryl and alkyl) afford 1-naphthols bearing 3,4-fused nitroxy rings, whereas their terminal alkyne analogous (R = H) deliver 1-naphthols with 2,3-fused nitroxy rings. Our DFT study confirms the intermediacy of α-oxo-gold carbenes that trap the tethered allenes to generate gold-containing 1,3-dipole-like species before [3 + 3]-annulations with a second nitrone. Our preliminary results indicate that quinoline oxides also generate similar gold-enolate containing 1,3-dipole-like intermediates Int-4 for further [3 + 3]-annulations.
AB - Gold-catalyzed nitrone oxidations of 1,5-allenynes are postulated to involve the formation of gold-enolate containing all carbon 1,3-dipole-like species Int-4, further yielding 1-naphthols fused with a nitroxy ring. 1,5-Allenynes bearing internal alkynes (R = aryl and alkyl) afford 1-naphthols bearing 3,4-fused nitroxy rings, whereas their terminal alkyne analogous (R = H) deliver 1-naphthols with 2,3-fused nitroxy rings. Our DFT study confirms the intermediacy of α-oxo-gold carbenes that trap the tethered allenes to generate gold-containing 1,3-dipole-like species before [3 + 3]-annulations with a second nitrone. Our preliminary results indicate that quinoline oxides also generate similar gold-enolate containing 1,3-dipole-like intermediates Int-4 for further [3 + 3]-annulations.
UR - http://www.scopus.com/inward/record.url?scp=85183023203&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85183023203&partnerID=8YFLogxK
U2 - 10.1021/acscatal.3c05620
DO - 10.1021/acscatal.3c05620
M3 - Article
AN - SCOPUS:85183023203
SN - 2155-5435
VL - 14
SP - 1525
EP - 1531
JO - ACS Catalysis
JF - ACS Catalysis
IS - 3
ER -