Copper-Catalyzed Chan–Lam Coupling between Sulfonyl Azides and

Letter pubs.acs.org/OrgLett

Copper-Catalyzed Chan−Lam Coupling between Sulfonyl Azides and Boronic Acids at Room Temperature Soo-Yeon Moon, Jungsoo Nam, Kris Rathwell, and Won-Suk Kim* Department of Chemistry and Nano Science, Ewha Womans University, Global Top 5 Program, Seoul 120-750, Korea S Supporting Information *

ABSTRACT: A mild and efficient method for the synthesis of N-arylsulfonamides in the presence of 10 mol % of CuCl is demonstrated. The reaction proceeds readily at room temperature in an open flask using a variety of sulfonyl azides and boronic acids without any base, ligand, or additive.

Table 1. Optimization of the N-Arylation Reaction of Phenylboronic Acid 1a with Tosyl Azide 2a

N-Arylsulfonamides are a common moiety present in a large number of pharmaceutically interesting compounds (Figure

Figure 1. N-Arylsulfonamide-containing drugs.

Scheme 1. Synthesis of N-Arylsulfonamides

entry

Cu cat.

solvent

time (h)

yieldb (%)

1 2 3 4 5 6 7 8 9 10 11 12 13

Cu(OAc)2 CuO CuCl2 Cul CuBr Cu2O CuBr S(Me)2 CuCl CuClc CuCld none CuCl CuCl

MeOH MeOH MeOH MeOH MeOH MeOH MeOH MeOH MeOH MeOH MeOH THF CH2Cl2

3 24 24 24 3 24 2 1 1 1 24 24 24

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