Abstract
New carbon–carbon bond formation reactions expand our horizon of retrosynthetic analysis for the synthesis of complex organic molecules. Although many methods are now available for the formation of C(sp2)–C(sp3) and C(sp3)–C(sp3) bonds via transition metal-catalyzed cross-coupling of alkyl organometallic reagents, direct use of readily available olefins in a formal fashion of hydrocarbonation to make C(sp2)–C(sp3) and C(sp3)–C(sp3) bonds remains to be developed. Here we report the discovery of a general process for the intermolecular reductive coupling of unactivated olefins with alkyl or aryl electrophiles under the promotion of a simple nickel catalyst system. This new reaction presents a conceptually unique and practical strategy for the construction of C(sp2)–C(sp3) and C(sp3)–C(sp3) bonds without using any organometallic reagent. The reductive olefin hydrocarbonation also exhibits excellent compatibility with varieties of synthetically important functional groups and therefore, provides a straightforward approach for modification of complex organic molecules containing olefin groups.
Highlights
New carbon–carbon bond formation reactions expand our horizon of retrosynthetic analysis for the synthesis of complex organic molecules
Olefin groups are widely represented in natural products with complex structures and many functional groups
We report the discovery of a new catalytic reaction of olefins, namely, Ni-catalyzed intermolecular reductive olefin hydrocarbonation between olefins and alkyl/aryl halides in an anti-Markovnikov fashion
Summary
New carbon–carbon bond formation reactions expand our horizon of retrosynthetic analysis for the synthesis of complex organic molecules. Use of olefins to replace alkylmetallic reagents in traditional crosscoupling reaction fashion25 (for example, Kumada coupling reaction) with aryl/alkyl electrophiles would have appealing advantages such as better functional group compatibility and broader substrate availability. A variety of carbon electrophiles and olefins with different functional groups could be readily converted to the desired products with modest to excellent yields (30–93%).
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