TY - JOUR
T1 - Distinct Selectivity of 2-Aryl Thioquinazolinones in the Sulfur Directing Rh(III)-Catalyzed Amidation Reaction
AU - Park, Keunju
AU - Min, Jeonghyun
AU - Kumar, Anand
AU - Lee, Youngil
AU - Kim, Youyoung
AU - Mishra, Neeraj Kumar
AU - Singh, Pargat
AU - Kim, In Su
N1 - Publisher Copyright:
© 2025 American Chemical Society.
PY - 2025/6/20
Y1 - 2025/6/20
N2 - Sulfur-directed C-H functionalization of N-heterocycles has emerged as an alternative solution to weakly coordinating carbonyl directing groups. In this study, we describe a sulfur-promoted Rh(III)-catalyzed C5 amidation of 4-thioquinazolinones using dioxazolones, yielding 5-amido-4-thioquinazolinones. The synthetic utility was demonstrated through a gram-scale experiment and synthetic modifications of the title compounds. A series of mechanistic investigations, including competition experiments, elucidated the effectiveness of the sulfur directing group in this process.
AB - Sulfur-directed C-H functionalization of N-heterocycles has emerged as an alternative solution to weakly coordinating carbonyl directing groups. In this study, we describe a sulfur-promoted Rh(III)-catalyzed C5 amidation of 4-thioquinazolinones using dioxazolones, yielding 5-amido-4-thioquinazolinones. The synthetic utility was demonstrated through a gram-scale experiment and synthetic modifications of the title compounds. A series of mechanistic investigations, including competition experiments, elucidated the effectiveness of the sulfur directing group in this process.
UR - https://www.scopus.com/pages/publications/105007688479
U2 - 10.1021/acs.joc.5c00952
DO - 10.1021/acs.joc.5c00952
M3 - Article
AN - SCOPUS:105007688479
SN - 0022-3263
VL - 90
SP - 8366
EP - 8375
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 24
ER -