Tetrahedron
Tetrahedron
5 years ago

Specific intramolecular aromatic CH insertion of diazosulfonamides

Specific intramolecular aromatic CH insertion of diazosulfonamides
The chemoselectivity in the intramolecular CH insertion of various diazosulfonamides has been experimentally studied. The results reveal that the aliphatic 1,4-, 1,5-, or 1,6-C(sp3)−H insertions of diazosulfonamides are not accessible, while the aromatic 1,5-C(sp2)−H insertion can be realized specifically by adjusting the diazo-adjacent group. In addition, the general chemoselectivities in the intramolecular CH insertions of diazosulfonyl compounds are summarized. Generally, diazosulfones undergo both aromatic 1,5-C(sp2)−H and aliphatic 1,5- and 1,6-C(sp3)−H insertions, while diazosulfonates undergo aliphatic 1,5- and 1,6-C(sp3)−H insertions. However, diazosulfonamides only undergo aromatic 1,5-C(sp2)−H insertion.

Publisher URL: www.sciencedirect.com/science

DOI: S0040402017304489

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