Copper-Catalyzed N-Arylation of Sulfoximines with Arylboronic Acids under Mild Conditions

Abstract

N-Arylation of sulfoximines with different arylboronic acids, including sterically hindered boronic acids, is achieved using copper(I) iodide and 4-DMAP at room temperature. Moreover, N-arylation of biologically relevant l-methionine sulfoximine is demonstrated for the first time. All these reactions provided the desired products in excellent yields within a short span of time. The optimized reaction conditions are well suited to the task of N-vinylation of sulfoximine with trans-2-phenylvinylboronic acid.

Functionalization of superparamagnetic Fe3O4@SiO2nanoparticles with a Cu(II) binuclear Schiff base complex as an efficient and reusable nanomagnetic catalyst forN‐arylation of α‐amino acids and nitrogen‐containing heterocycles with aryl halides

“…[7,8] The first copper catalyzed C-N bond formation was developed by Ullman and Goldberg. [9,10] Various types of N-arylation have been reported in the literature that some examples come as follows: N-arylation of imidazoles, [11][12][13][14][15][16] Cu(I)-catalyzed N-arylation of indoles, [17] C-N coupling of aniline with terminal alkynes (synthesis of α-ketoamides), [18] copper-mediated C-N coupling reaction of azido compounds and aryl halides, [19] N-arylation of aryl halides with alkyl amine using CuBr catalyst which benefits from phosphoramidite as a ligand, [20] Cu(I)-catalyzed N-arylation of pyrazoles, [21] N-arylation of aryl iodide with hypervalent aryl siloxanes by Cu (OAc) 2 along with a ligand, [22] N-arylation of α-amino acids catalyzed by Cu(I), [23][24][25] cross-coupling reaction of aryl halides to aryl amines catalyzed by Cu 2 O in solution of ammonia, [26] N-alkynylation of amides catalyzed by Cu(I), [27] Cu(I)-amidation catalyzed of aryl halides, [28][29][30] Ullmann-type N-arylation of anilines, [31] Cu-catalyzed intramolecular adjacent C-N coupling (asymmetric synthesis of atropisomeric compounds), [32] Cu/N,N 0dibenzyloxalamide-catalyzed N-arylation of heteroanilines, [33] Cu-catalyzed N-arylation of sulfoximines, [34] Cu-catalyzed decarboxylative N-arylation of indole-2-carboxylic acids, [35] and Cu-catalyzed intramolecular benzylic C-H amination for the synthesis of isoindolinones. [36] Magnetic nanoparticles (MNs) are a class of nanoparticles which include magnetic elements (commonly Fe, Ni, or Co or their combinations), [37,38] but they suffer from agglomeration phenomena due to large interaction between nanoparticles arising from their nano-size and high aspect ratio.…”

Syntheses and Transformations of Sulfoximines

“…In addition, for the first time, they obtained the biologically related N‐aryl L‐methionine sulfoximines (Scheme 30, eqn. b) [64] …”

Facile synthesis of N-1,2,4-oxadiazole substituted sulfoximines from N-cyano sulfoximines

“…3 In contrast to a sulfone, the sulfoximine group has an additional site that could be functionalized at the NH bond. Introduction of groups such as trifluoromethyl, 6h alkyl, 6c,s acyl, 6d,r alkynyl, 6j,l-n allyl, 6k alkenyl, 6p,q sulfenyl, 6b phosporyl, 6a silyl, 6f cyano, 6g,o aryl 7 and heteroaryl 8 at the nitrogen atom of sulfoximine has been well documented in the sulfoximine literature. [6][7][8] Among these, the synthesis of N-arylsulfoximines has attracted a wider attention.…”

“…Introduction of groups such as trifluoromethyl, 6h alkyl, 6c,s acyl, 6d,r alkynyl, 6j,l-n allyl, 6k alkenyl, 6p,q sulfenyl, 6b phosporyl, 6a silyl, 6f cyano, 6g,o aryl 7 and heteroaryl 8 at the nitrogen atom of sulfoximine has been well documented in the sulfoximine literature. [6][7][8] Among these, the synthesis of N-arylsulfoximines has attracted a wider attention. There are relatively fewer reports that describe the synthesis of N-heteroaryl sulfoximines despite their potential utility in medicinal chemistry 3,9 and agro applications.…”