Synthesis of structurally diversified BINOLs and NOBINs via palladium-catalyzed C-H arylation with diazoquinones

Ji-Wei Zhang1; Fei Jiang; Ye-Hui Chen; Shao-Hua Xiang3; Bin Tan

2021

Science China-Chemistry   Impact Factor & Quartile

1674-7291

Privileged biaryl frameworks,BINOL and NOBIN,were efficiently constructed with sole 1-DNQs as arylation reagents under one set of reaction conditions.The judicious selection of palladium-catalytic system plays a pivotal role in the excellent selectivities.This transformation accommodated fairly broad substrate generality for both 2-naphthol and N-Boc-2-naphthy-lamine and afforded the structurally diversified BINOLs and NOBIN derivatives in high efficiency.Notably,the bromo-substituents which cannot survive in conventional palladium-catalyzed reactions were well-compatible with this set of condi-tions,providing an effective handle for further enriching the library of BINOLs and NOBINs.Preliminary attempts on the asymmetric variant of this reaction were also performed with up to 80:20 er for BINOLs synthesis.

English

First

WanFang

zgkx-eb202109012

1.School of Chemistry and Chemical Engineering,Harbin Institute of Technology,Harbin 150001,China;Shenzhen Grubbs Institute and Department of Chemistry,Southern University of Science and Technology,Shenzhen 518055,China
2.Shenzhen Grubbs Institute and Department of Chemistry,Southern University of Science and Technology,Shenzhen 518055,China
3.Shenzhen Grubbs Institute and Department of Chemistry,Southern University of Science and Technology,Shenzhen 518055,China;Academy for Advanced Interdisciplinary Studies,Southern University of Science and Technology,Shenzhen 518055,China

Ji-Wei Zhang,Fei Jiang,Ye-Hui Chen,et al. Synthesis of structurally diversified BINOLs and NOBINs via palladium-catalyzed C-H arylation with diazoquinones[J]. Science China-Chemistry,2021,64(9):1515-1521.

Ji-Wei Zhang,Fei Jiang,Ye-Hui Chen,Shao-Hua Xiang,&Bin Tan.(2021).Synthesis of structurally diversified BINOLs and NOBINs via palladium-catalyzed C-H arylation with diazoquinones.Science China-Chemistry,64(9),1515-1521.

Ji-Wei Zhang,et al."Synthesis of structurally diversified BINOLs and NOBINs via palladium-catalyzed C-H arylation with diazoquinones".Science China-Chemistry 64.9(2021):1515-1521.