Three-component cross-coupling reactions involving alkenes enabled by visible-light and earth-abundant-metal-catalysis

Catalytic difunctionalizations of alkenes represent one of the most straightforward and efficient ways to build molecular complexity due to the simultaneous installation of two vicinal chemical bonds onto alkenes, providing profound chemical space for selective transformations in organic synthesis. Over the past decade, the merge of visible-light catalysis and earth-abundant-metal catalysis has taken advantage of green catalysis, thus evolving into an enabling platform for difunctionalization of alkenes. This dual catalytic mode facilitates the construction of multiple chemical bonds over the π-bond of alkenes in one step, providing a mild and straightforward method for the rapid construction of sp³-rich structures in a selective manner. In this review, we systematically summarized the progress of three-component cross-coupling reaction of olefins catalyzed by visible light and first-row transition-metal over the past decade. The combination of visible-light with different first-row transition metals, such as copper, nickel, chromium, titanium, manganese and iron, are discussed as well as the detailed reaction mechanisms. The scope of alkenes in this review includes alkenes, 1,3-dienes and 1,3-enynes. Moreover, the future directions and efforts in visible-light and earth-abundant-metal-catalyzed three-component reaction of alkenes are also discussed.