17075-25-1Relevant articles and documents
Understanding Mechanistic Differences between 3-Diazoindolin-2-Imines and N-Sulfonyl-1,2,3-Triazoles in the Rh2(II)-Catalyzed Reactions with Nitrosoarenes
Bao, Xiaoguang,Fu, Rui,Gao, Ke,Kou, Luyao,Zhou, Shaofang
supporting information, p. 1565 - 1572 (2021/05/28)
The employment of α-iminometallocarbenes to construct valuable N-containing compounds has attracted significant research interest. Herein, the nucleophilic addition of nitrosoarenes with the α-imino rhodium carbene species (I), which is derived from Rh2(II)-catalyzed denitrogenation of 3-diazoindolin-2-imines, to produce synthetically useful 2-iminoindolin-nitrones is described. Mechanistically, the N-attack of nitrosoarenes with the carbene site of I is proposed. For the analogous Rh2(II)-catalyzed reaction of nitrosoarenes with N-sulfonyl-1,2,3-triazoles reported by Li and co-workers (Org. Lett. 2014, 16, 6394), however, the O-attack of nitrosoarenes with the carbene site of α-imino rhodium carbene species (II) is more favorable to occur than the N-attack. The subsequent transformation to yield the product of N-acylamidines is rationalized based on computational studies. The mechanistic differences for the reactions of nitrosoarenes with α-imino rhodium carbene species I and II are discussed.
Synthesis of N -acylamidines via rhodium-catalyzed reaction of nitrosobenzene derivatives with N -sulfonyl-1,2,3-triazoles
Ran, Rui-Qiao,Xiu, Shi-Dong,Li, Chuan-Ying
supporting information, p. 6394 - 6396 (2015/02/18)
α-Imino rhodium carbene, readily generated from N-sulfonyl-1,2,3-triazole, underwent cycloaddition and subsequent rearrangement with a nitrosobenzene derivative to afford N-acylamidine. The unprecedented C-C bond cleavage of α-imino carbene was facilitated by the weakness of the N-O bond.
