The unique reactivity of trans-cycloalkenes has recently produced an impressive resume of applications in synthesis, including reactions with dienes, 1,3-dipoles and ketenes, and strained trans-cycloalkenes can serve as excellent ligands for transition metals. In addition to their usefulness in synthesis, trans-cycloalkenes hold special significance in the field of bioorthogonal chemistry due to their particularly fast kinetics in reactions with tetrazines. Herein we described a procedure for driving photochemical sytheses of trans-cycloheptene and sila trans-cycloheptene derivatives through metal complexation. The synthetic application of trans-cycloheptene and sila trans-cycloheptene derivatives were explored. Sila trans-cycloheptene displays enhance reactivity in the tetrazine ligation. Cell imagine experiment was performed with sila trans-cycloheptene halotag derivative which was stabilized as a metal complex as well as sila trans-cycloheptene BODIPY metal complex. The second order rate constant was measured for the sila trans-cycloheptene and dipyridyl-1,2,4,5-tetrazine, which to the best of our knowledge, makes this the fastest conjugation rate measurement to date.

Trans-cycloheptene, sila trans-cycloheptene and their application in bioorthogonal chemistry

253rd National Meeting (2017)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.