Shen, Xiaoqiang; Jones, Gavin O.; Watson, Donald A.; Bhayana, Brijesh; Buchwald, Stephen L. published the artcile< Enantioselective Synthesis of Axially Chiral Biaryls by the Pd-Catalyzed Suzuki-Miyaura Reaction: Substrate Scope and Quantum Mechanical Investigations>, Reference of 16426-64-5, the main research area is enantioselective preparation axially chiral biaryl; palladium catalyzed Suzuki Miyaura substrate scope quantum mech crystallog.
The authors report efficient syntheses of axially chiral biaryl amides in yields ranging from 80-92%, and with enantioselectivity in the range 88-94% ee employing an asym. Suzuki-Miyaura process with Pd(OAc)2 and KenPhos as ligand. Electron-rich and electron-deficient o-halobenzamides can be efficiently coupled with 2-methyl-1-naphthylboronic acid and 2-ethoxy-1-naphthylboronic acid. The yields and selectivities of the reactions are independent of the nature of halogen substituent on the benzamide coupling partner. Studies demonstrate that axially chiral heterocyclic and biphenyl compounds can also be synthesized with this methodol. The authors also report computational studies used to determine the origin of stereoselectivity during the selectivity-determining reductive elimination step of the related coupling of tolylboronic acid with naphthylphosphonate bromide that was reported in a previous publication. The stereoselectivity arises from a combination of weak -(C)H··O interactions as well as steric interactions between the tolyl and naphthylphosphonate addends in the transition state for C-C coupling.
Journal of the American Chemical Society published new progress about Amides Role: PEP (Physical, Engineering or Chemical Process), RCT (Reactant), PROC (Process), RACT (Reactant or Reagent). 16426-64-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrNO4, Reference of 16426-64-5.
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary