TY - JOUR
T1 - Gold(I/III)-Catalyzed Sulfonylation of Aryl/Vinyl Iodides To Synthesize Aryl Sulfones
AU - Zhang, Lizhu
AU - Du, Wenqian
AU - Wu, Jiawen
AU - Yang, Rongjie
AU - Zhao, Fen
AU - Fan, Baomin
AU - Xia, Zhonghua
N1 - Publisher Copyright:
© 2024 American Chemical Society.
PY - 2025/1/10
Y1 - 2025/1/10
N2 - A gold-catalyzed sulfonylation of aryl/vinyl iodides to synthesize aryl sulfones facilitated by the ligand-enabled Au(I)/Au(III) redox catalysis was developed. In the reaction, aryl sodium sulfinates or sulphinic acids can react smoothly with aryl/vinyl iodides to directly construct various aryl sulfones. The strong synthetic capabilities of sulfone synthesis are demonstrated by its easily available and handled reagents, good functional group compatibility, and late-stage application of complicated biomolecules. Mechanistic studies suggest that the silver salt plays a crucial role in the transmetalation with the Au(I)/Au(III) intermediate, and the gold complex favors Au-S bond formation over Au-O bond formation.
AB - A gold-catalyzed sulfonylation of aryl/vinyl iodides to synthesize aryl sulfones facilitated by the ligand-enabled Au(I)/Au(III) redox catalysis was developed. In the reaction, aryl sodium sulfinates or sulphinic acids can react smoothly with aryl/vinyl iodides to directly construct various aryl sulfones. The strong synthetic capabilities of sulfone synthesis are demonstrated by its easily available and handled reagents, good functional group compatibility, and late-stage application of complicated biomolecules. Mechanistic studies suggest that the silver salt plays a crucial role in the transmetalation with the Au(I)/Au(III) intermediate, and the gold complex favors Au-S bond formation over Au-O bond formation.
UR - http://www.scopus.com/inward/record.url?scp=85212553305&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.4c01675
DO - 10.1021/acs.joc.4c01675
M3 - Article
AN - SCOPUS:85212553305
SN - 0022-3263
VL - 90
SP - 44
EP - 51
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 1
ER -