Copper-catalyzed N–H insertion reactions from sulfoxonium ylides

Cooperative copper-squaramide catalysis for the enantioselective N–H insertion reaction with sulfoxonium ylides

“… 17 Therefore we commenced our studies by screening different organocatalysts in our optimized conditions recently published for the racemic version of the reaction. 36 The main results are depicted in Scheme 2 (for full optimization tables see ESI † ). Using quinine ( Q1 ) as organocatalyst, product 3 was formed with 63 : 37 e.r.…”

“…Very recently, our group demonstrated that the use of inexpensive copper(II) salts is also efficient for insertion reactions (N-H) with sulfur ylides. 36 Despite these important contributions, the rst two enantioselective versions of X-H insertions were reported only last yearthe rst of which was developed by our research group in collaboration with the Mattson group, based on asymmetric S-H insertions with sulfoxonium ylides and arylthiols, catalysed by a chiral thiourea 37 (Scheme 1a). The second, describes a chiral phosphoric acid catalysed N-H insertion in the presence of anilines and sulfonium ylides 38 by Sun (Scheme 1b).…”

“…Very recently, our group demonstrated that the use of inexpensive copper( ii ) salts is also efficient for insertion reactions (N–H) with sulfur ylides. 36 …”

Asymmetric transformations from sulfoxonium ylides

“…Metal-carbenes from sulfoxonium ylides have been employed in several insertion reactions, such as into X-H (N, O, S, B, P) and C-H bonds (Scheme 2D and E). [20][21][22][23][24][25] These ylides can also participate in cross-coupling reactions by metal-carbene migratory insertion, resulting in C-H activation processes mediated mainly by the M(III) catalysts. 26,27 From the products provided in the C-H activation step, many post functionalization reactions can be performed to generate structurally diverse heterocycles and carbocycles (Scheme 2F and G).…”

Recent Advances in Metal‐Catalyzed C−H Bond Functionalization Reactions of Sulfoxonium Ylides

“…proposed an efficient Cu‐catalyzed N−H insertion reaction of aniline with sulfoxonium ylide and synthesized arylglycine and N ‐aryl amino acids derivatives (Scheme 67). [72a] They extended their work using chiral bifunctional squaramide cooperative catalyst and synthesized enantioselective N−H insertion reaction from aniline and sulfoxonium ylide (Scheme 68). [72b] …”