TY - JOUR
T1 - Addition, Substitution, and Ring-Contraction Reactions of Quinones with N-Heterocyclic Carbenes
AU - Ping, Lucy
AU - Bak, Jungmin
AU - Kim, Youngmee
AU - Bouffard, Jean
N1 - Funding Information:
This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (Grant 2015R1D1A1A01059383). We thank Dr. Hea Kyoung Lee of the Organic Chemistry Research Center at Sogang University for ESI-MS analyses.
Publisher Copyright:
© 2018 American Chemical Society.
PY - 2018/8/17
Y1 - 2018/8/17
N2 - Despite the common use of quinones as oxidizing agents in N-heterocyclic carbene (NHC)-based organocatalysis and transition-metal catalysis, the direct reactivity of quinones with NHCs remains underexplored. In this paper, we report the reactivity of NHCs with common p- and o-quinones, uncovering three unreported reactions involving contractions of the quinone ring that lead to push-pull furanolactone chromophores, NHC fulvalenes, and α-acylimidazolium cyclopentenone derivatives. These experiments also provide a rationale for the superior compatibility of tetra-tert-alkylated diphenoquinones in NHC-based oxidative transformations.
AB - Despite the common use of quinones as oxidizing agents in N-heterocyclic carbene (NHC)-based organocatalysis and transition-metal catalysis, the direct reactivity of quinones with NHCs remains underexplored. In this paper, we report the reactivity of NHCs with common p- and o-quinones, uncovering three unreported reactions involving contractions of the quinone ring that lead to push-pull furanolactone chromophores, NHC fulvalenes, and α-acylimidazolium cyclopentenone derivatives. These experiments also provide a rationale for the superior compatibility of tetra-tert-alkylated diphenoquinones in NHC-based oxidative transformations.
UR - http://www.scopus.com/inward/record.url?scp=85051747992&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.8b01236
DO - 10.1021/acs.joc.8b01236
M3 - Article
C2 - 29932338
AN - SCOPUS:85051747992
SN - 0022-3263
VL - 83
SP - 9240
EP - 9249
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 16
ER -