128753-03-7Relevant articles and documents
Rh(III)-Catalyzed Chemodivergent Annulations between Indoles and Iodonium Carbenes: A Rapid Access to Tricyclic and Tetracyclic N-Heterocylces
Kanchupalli, Vinaykumar,Kumar, Sanjeev,Nanduri, Srinivas,Nunewar, Saiprasad,Pandhare, Harishchandra
, p. 4233 - 4238 (2021)
Herein, we report an acid-controlled highly tunable selectivity of Rh(III)-catalyzed [4 + 2] and [3 + 3] annulations of N-carboxamide indoles with iodonium ylides lead to form synthetically important tricyclic and tetracyclic N-heterocycles. Here, iodonium ylide serves as a carbene precursor. The protocol proceeds under operationally simple conditions and provides novel tricyclic and tetracyclic scaffolds such as 3,4-dihydroindolo[1,2-c]quinazoline-1,6(2H,5H)-dione and 1H-[1,3]oxazino[3,4-a]indol-1-one derivatives with a broad range of functional group tolerance and moderate to excellent yields. Furthermore, the protocol synthetic utility was extended for various chemical transformations and was easily scaled up to a large-scale level.
A relationship between the catalytic carbonylation of (N-arenesulfonyl)imides and iodonium ylides
Besenyei,Neszmelyi,Holly,Simandi,Parkanyi
, p. 649 - 654 (2001)
Reactivities of various sulfonamide derivatives of general formula ArSO2N=XPhn (X = I; n = 1; X = S, Se, n = 2; X = P, As, n = 3) in catalytic carbonylations have been explained by structural properties of the substrates. Based on cr
1,3-Carboboration of iodonium ylides
Gazis, Theodore A.,Mohajeri Thaker, Bayan A. J.,Willcox, Darren,Ould, Darren M. C.,Wenz, Jan,Rawson, Jeremy M.,Hill, Michael S.,Wirth, Thomas,Melen, Rebecca L.
supporting information, p. 3345 - 3348 (2020/04/02)
Herein, we disclose the utilisation of iodonium ylides to access a range of boron dienolates. Heating of acyclic iodonium ylides in the presence of different aryl boranes leads to the formation of rare 1,3-carboboration products. This methodology could not be expanded to cyclic iodonium ylides which instead formed a Lewis acid-base adduct. Products proved to be remarkably stable under a wide range of conditions allowing for their long term storage.
Transition-metal-free approach to synthesis of indolines from N-(ortho-chloromethyl)aryl amides and iodonium ylides
Huang, Hui,Yang, Yuan,Zhang, Xiaoyun,Zeng, Weilan,Liang, Yun
supporting information, p. 6049 - 6052 (2013/10/22)
A transition-metal-free method for the synthesis of indolines has been developed. In the presence of K2CO3, the cyclization reaction of N-(ortho-chloromethyl)aryl amides and iodonium ylides proceeded smoothly at room temperature in moderate to good yields.
Reaction of iodonium ylides of 1,3-dicarbonyl compounds with HF reagents
Gondo, Keisuke,Kitamura, Tsugio
scheme or table, p. 6625 - 6632 (2012/08/27)
Reaction of dibenzoylmethane with (diacetoxyiodo)benzene in the presence of KOH in MeCN quantitatively gave the corresponding iodonium ylide, which was treated with a HF reagent to afford the corresponding 2-fluorinated dibenzoylmethane in 14-50% yields.
