Studies On The H-phosphonates Mediated Construction Of C-C/C-N Bonds

C-C and C-N bonds are widely present in organic compounds such as natural products,pesticides,and pharmaceutical intermediates.Thus it has always been a scientific focus to construct C-C and C-N bonds via simple,green,efficient,and economical methods.Nitrogen-containing aromatic compounds are widely exsited in the structure of active pharmaceutical molecules and organic materials,the synthesis of those compounds has always been a focus of attention.Unsymmetrical amines(secondary and tertiary amines),an important class of amines,act as important building blocks in natural products,drugs and functional materials.This H-phosphonate mediated reaction realize the construction of C-C bond in high selectivity and synthesis of series of functionalized nitrogen-containing aromatic compounds;and also realize the construction of C-N bond effectively and synthesis of a large number of polyamines.The contents and the results come as follows:(1)A highly selective simple H-phosphonate mediated C-C bond formation via cross coulping has been disclosed.With the cooperation of H-phosphonate and catalytic amount of KI,diphenylamines,indoles,naphthylamines and carbazoles can react with cumenes smoothly,and synthesis of a variety of novel functionalized nitrogen-containing aromatic compounds with high selectivity in a simple and environmentally friendly way.(2)An effecient and simple H-phosphonate mediated C-N bond formation via N-alkylation of amines with alcohols to afford polyamines has been achieved.Except H-phosphonate,transition-metal catalysts,additional acids,bases,and oxidants,even solvent,are not required at all.This reaction features good functional groups compatibility and tolerance.Both electron-donating and electron-withdrawing groups were tolerable,affording the corresponding products in good to excellent yields.The reaction conditions are simple,green,and have potential application value in the field of synthesis.