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Herein, we report a novel photoinduced homologative 1,3\u2010dicarbofunctionalization of unactivated alkenes via one\u2010carbon chain elongation, achieved through sequential functional group migrations. By employing strategically designed tertiary alcohols and heteroarylsulfones as versatile coupling partners, this method affords structurally diverse, densely substituted aliphatic ketones and medium\u2010sized cyclic scaffolds with exclusive chemo\u2010 and regioselectivity. 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