Next, we investigated the gem-difluoroallylation of cyclohexane with various α-trifluoromethyl alkene partners. As depicted in Scheme 2B, this visible light induced synergistic W/Cr catalyzed gem-difluoroallylation reaction tolerated a diverse set of functional groups on the phenyl ring of α-trifluoromethyl styrenes, including aryl (3aa), ether (3ab-3ae), protected amine (3af, 3ag), amide (3ah, 3ai), and ester (3aj), and the corresponding gem-difluoroalkenes were attained in moderate to high yields (33-80%). It was found that the reaction was sensitive to both electronic and steric characters of the substituents on the phenyl ring. Substrates with an electron-withdrawing group delivered higher yields compared with those with an electron-donating group (3ab vs 3ac, 3af vs 3ag), and orthosubstituted substrate gave rise to significantly diminished reactivity (3ad). Notably, the unprotected amide group was compatible with this transformation, furnishing product 3ai in 56% yield. α-trifluoromethyl styrenes containing polycyclic and heterocyclic arene substituents, such as naphthalene (3ak), dibenzothiophene (3al), dibenzofuran (3am), and quinoline (3an), were competent coupling partners. Apart from α-trifluoromethyl styrene, α-trifluoromethyl eneyne was also readily accommodated to furnish product 3ao in 45% yield. Notably, α-trifluoromethyl styrenes with an electron-withdrawing group, hydroalkylation reaction pathway was also possible to give a mixture of gem-difluoroalkenes and trifluoromethyl compounds (3ai, 3aj, 3an), and in the case of strongly electron-deficient formyl-substituted substrate, the trifluoromethyl compound 4ap was isolated as the major product.