Nucleophilic Alkoxylations of Unactivated Alkyl Olefins and ??Methyl Styrene by Photoredox Catalysis

Hydromethylation of Unactivated Olefins

A solution to the classic unsolved problem of olefin hydromethylation is presented. This highly chemoselective method can tolerate labile and reactive chemical functionalities and uses a simple set of reagents. An array of olefins, including mono-, di-, and trisubstituted olefins, are all smoothly hydromethylated. This mild protocol can be used to simplify the synthesis of a specific target or ...

Photoredox Imino Functionalizations of Olefins

Shown herein is that polyfunctionalized nitrogen heterocycles can be easily prepared by a visible-light-mediated radical cascade process. This divergent strategy features the oxidative generation of iminyl radicals and subsequent cyclization/radical trapping, which allows the effective construction of highly functionalized heterocycles. The reactions proceed efficiently at room temperature, uti...

Direct alkylation of heteroarenes with unactivated bromoalkanes using photoredox gold catalysis

Although visible light photoredox catalysis has emerged as a powerful tool for the construction of C–C bonds, common catalysts and/or their photoexcited states suffer from low redox potentials, limiting their applicability to alkyl radical generation from substrates with activated carbon–halogen bonds. Radicals derived from these activated compounds, being highly electrophilic or stabilized, do...

Alkyl-alkyl Suzuki cross-coupling of unactivated secondary alkyl chlorides.

The first method for achieving alkyl–alkyl Suzuki reactions of unactivated secondary alkyl chlorides has been developed. Carbon–carbon bond formation occurs under mild conditions (at room temperature) with the aid of commercially available catalyst components. This method has proved to be versatile: without modification, it can be applied to Suzuki reactions of secondary and primary alkyl bromi...

Allylic C-H alkylation of unactivated α-olefins: serial ligand catalysis resumed.