Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

Supramolecular Construction of an Aldehyde–Cyclobutane via the Solid State: Combining Reversible Imine Formation and Metal–Organic Self-Assembly

Supramolecular Construction of an Aldehyde–Cyclobutane via the Solid State: Combining Reversible Imine Formation and Metal–Organic Self-Assembly
Leonard R. MacGillivray, Shalisa M. Oburn, S. V. Santhana Mariappan, Dale C. Swenson
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 geometry 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 quantitative yield. Removal of the pyridyl group affords the aldehyde-functionalized cyclobutane α-truxilaldehyde.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b04420

DOI: 10.1021/jacs.7b04420

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