39835-11-5Relevant articles and documents
para-Selective Arylation of Arenes: A Direct Route to Biaryls by Norbornene Relay Palladation
Dutta, Uttam,Grover, Jagrit,Koodan, Adithyaraj,Maiti, Debabrata,Mandal, Astam,Pimparkar, Sandeep,Porey, Sandip
, p. 20831 - 20836 (2020)
Biaryl compounds are extremely important structural motifs in natural products, biologically active components and pharmaceuticals. Selective synthesis of biaryls by distinguishing the subtle reactivity difference of distal arene C?H bonds are significantly challenging. Herein, we describe para-selective C?H arylation, which is acheived by a unique combination of a meta-directing group and norbornene as a transient mediator. Upon direct meta-C?H palladation, one-bond relay palladation occurs in presence of norbornene and subsequently para-C?H arylation is achieved for sulfonates, phosphonates and phenols bearing 2,6-disubstitution patterns. The protocol is amenable to electron-deficient aryl iodides. Multisubstituted arenes and phenols are obtained by postsynthetic modification of the products. The protocol allows the synthesis of hexa-substituted benzene by sequential selective distal C?H functionalization.
Rhodium-Catalyzed meta-C?H Functionalization of Arenes
Bera, Milan,Agasti, Soumitra,Chowdhury, Rajdip,Mondal, Rahul,Pal, Debasis,Maiti, Debabrata
, p. 5272 - 5276 (2017/04/27)
Rhodium-catalyzed ortho-C?H functionalization is well known in the literature. Described herein is the Xphos-supported rhodium catalysis of meta-C?H olefination of benzylsulfonic acid and phenyl acetic acid frameworks with the assistance of a para-methoxy-substituted cyano phenol as the directing group. Complete mono-selectivity is observed for both scaffolds. A wide range of olefins and functional groups attached to arene are tolerated in this protocol.
Perfluoroalkanosulfonyl fluoride: A useful reagent for dehydration of aldoximes to nitriles
Yan, Zhao-Hua,Tian, Huan,Zhao, Dong-Dong,Jin, Hong-Ai,Tian, Wei-Sheng
, p. 96 - 98 (2016/01/25)
The reaction of a variety of aldoximes with perfluoroalkanosulfonyl fluoride in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in dichloromethane smoothly generated the corresponding nitriles in 70%-95% yields.