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Desulfonylative Arylation of Redox-Active Alkyl Sulfones with Aryl Bromides
Jonathan M E Hughes1, Patrick S Fier1
1Department of Process Research and Development , Merck & Co., Inc. , Rahway , New Jersey 07065 , United States.
Abstract:
We describe the development of the first reductive cross-electrophile coupling between alkyl sulfones and aryl bromides. The use of alkyl sulfones offers strategic advantages over other alkyl electrophiles as they can be incorporated into molecules in unique ways and permit α-functionalization prior to coupling. The conditions developed here enable incorporation of a wide array of aromatic rings onto (fluoro)alkyl scaffolds with broad functional group tolerance and generality, making this a practical method for late-stage diversification.
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Alkyl Halides
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
Electrophilic Aromatic Substitution: Sulfonation of Benzene