RT Journal Article
T1 Broad-Scope Amination of Aryl Sulfamates Catalyzed by a Palladium Phosphine Complex
A1 Monti, Andrea
A1 López Serrano, Joaquín
A1 Prieto Cárdenas, María Auxiliadora
A1 Nicasio Jaramillo, María Carmen
AB Among phenol-derived electrophiles, aryl sulfamates are attractive substrates since they can be employed as directing groups for C–H functionalization prior to catalysis. However, their use in C–N coupling is limited only to Ni catalysis. Here, we describe a Pd-based catalyst with a broad scope for the amination of aryl sulfamates. We show that the N-methyl-2-aminobiphenyl palladacycle supported by the PCyp2ArXyl2 ligand (Cyp = cyclopentyl; ArXyl2 = 2,6-bis(2,6-dimethylphenyl)phenyl) efficiently catalyzes the C–N coupling of aryl sulfamates with a variety of nitrogen nucleophiles, including anilines, primary and secondary alkyl amines, heteroaryl amines, N-heterocycles, and primary amides. DFT calculations support that the oxidative addition of the aryl sulfamate is the rate-determining step. The C–N coupling takes place through a cationic pathway in the polar protic medium.
PB American Chemical Society (ACS)
SN 2155-5435 (electrónico)
YR 2023
FD 2023-08
LK https://hdl.handle.net/10272/23297
UL https://hdl.handle.net/10272/23297
LA eng
NO Monti, A., López-Serrano, J., Prieto, A., & Nicasio, M. C. (2023). Broad-Scope Amination of Aryl Sulfamates Catalyzed by a Palladium Phosphine Complex. In ACS Catalysis (Vol. 13, Issue 16, pp. 10945–10952). American Chemical Society (ACS). https://doi.org/10.1021/acscatal.3c03166
NO We thank financial support from MCIN/AEI/10.13039/501100011033 (Grant PID2020-113797RB-C22), US/JUNTA/FEDER, UE (Grant US-1262266), and FEDER, UE/Junta de Andalucía-Consejería de Transformación, Economía, r Industria, Conocimiento y Universidades (Grant P20_00624) for financial support. A.M. thanks MICINN for a research fellowship. A.P. thanks Ministerio de Universidades (Plan de Recuperación Transformación y Resilencia) for financial support. The use of computational resources of the Universidad de Granada (cluster Albaicin) is thankfully acknowledged.
DS Repositorio Institucional de la Universidad de Huelva
RD 30 may 2026