Cyclization methods
The invention provides methods for cyclizing poly-yne compounds under mild conditions to provide cyclic compounds.
1. A method comprising cyclizing a compound including three triple bonds, wherein two of the triple bonds are in a conjugated butadiyne subunit at a temperature below about 300° C. to provide a polycyclic compound having four carbon atoms from the two triple bonds that were in the conjugated butadiyne subunit present in a six-membered carbocyclic ring of the polycyclic compound.
2. A method comprising cyclizing a nonaromatic compound including three triple bonds, wherein two of the triple bonds are in a conjugated butadiyne subunit at a temperature below about 300° C. to provide a polycyclic compound having four carbon atoms from the two triple bonds that were in the conjugated butadiyne subunit present in a six-membered carbocyclic ring of the polycyclic compound.
3. The method of claim 1 further comprising contacting the polycyclic compound with a benzyne trapping reagent.
4. The method of claim 3 wherein the benzyne trapping reagent is a phenol, a furan, cyclooctane, cycloheptane, an alcohol, benzene, or a substituted benzene derivative.
5. The method of claim 3 wherein the benzyne trapping reagent is an aromatic agent, a formal hydrogen molecule (H 2 ) donor, an oxygen-based nucleophile of protic or aprotic nature, a sulfur containing nucleophile, a selenium-containing nucleophile, a phosphorous-containing nucleophile, a nitrogen-containing nucleophile, a halogen source, a metal halide salt, a hydrogen halide, an ammonium halide, a halosilane, an alkyl halide, or a pi-bond cycloaddend.
6. A polycyclic compound prepared according to the method of claim 3 .