Light induced catalytic C—H oxygenation of alkanes

A method of modifying a benzylic C—H bond, thereby forming a compound represented by Formula 1:

• the method comprising:
• irradiating a reaction mixture comprising a substrate comprising said benzylic C—H bond, oxygen and an initiator with a light, thereby forming said compound, wherein:
• each X independently comprises an optionally substituted aromatic cycloalkane, an optionally substituted C3-C10 cycloalkane, or is absent;
• said light is in a wavelength range sufficient for exciting the initiator, thereby generating a halogen radical;
• represents any one of:
• (i) a single bond if n is 2;
• and (ii) a double bond if n is 1;
• X comprises an aromatic ring;
• R is selected from the group consisting of:
• an alkyl, an aryl, hydrogen, and a cycloalkyl;
• R1 is selected from the group consisting of:
• hydrogen, hydroxy, or is absent;
• and n is 1 or 2,
• wherein said initiator is represented by Formula 4:
• wherein
• each X independently comprises an optionally substituted aromatic cycloalkane, an optionally substituted C3-C10 cycloalkane, or is absent;
• and each A independently represents a halo group.