Journal of the American Chemical Society, Vol.139, No.25, 8452-8454, 2017
Supramolecular Construction of an Aldehyde-Cyclobutane via the Solid State: Combining Reversible Imine Formation and Metal-Organic Self-Assembly
A combination of Metal organic self assembly and reversible imine formation is used to achieve an organic synthesis via the solid state. Imine bond formation is employed to install a pyridyl to the alkene trans-cinnamaldehyde while Ag(I) ions are used in,a second step to assemble the pyridyl-functionalized alkene into a geothetry in the solid state for an intermolecular [2 + 2] photodimerization. The alkene undergoes the cycloaddition reaction via a 1D coordination polymer, to generate a pyridyl-functionalized cyclobutane stereoselectively and in quantitatfre yield. Removal of the pyridyl group affords the aldehyde-functionalized cyclobutane alpha-truxilaldehyde.