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Transition-Metal-Free C-Diarylations to Reach All-Carbon Quaternary Centers.

ABSTRACT: Herein, we disclose a convenient protocol for the α-diarylation of carbon nucleophiles to yield heavily functionalized quaternary products. Diaryliodonium salts are utilized to transfer both aryl groups under transition-metal-free conditions, which enables an atom-efficient and high-yielding method with broad functional group tolerance. The methodology is amenable to a wide variety of carbon nucleophiles and can be utilized in late-stage functionalization of complex arenes. Furthermore, it is compatible with a new class of zwitterionic iodonium reagents, which gives access to phenols with an ortho-quaternary center. The diarylated products bear an ortho-iodo substituent that can be utilized in further transformations, including the formation of novel, functionalized six-membered cyclic iodonium salts.

SUBMITTER: Mondal S

PROVIDER: S-EPMC11350576 | biostudies-literature | 2024 Aug

REPOSITORIES: biostudies-literature

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Transition-Metal-Free <i>C</i>-Diarylations to Reach All-Carbon Quaternary Centers.

Mondal Shobhan S Gunschera Benjamin B Olofsson Berit B

JACS Au 20240805 8

Herein, we disclose a convenient protocol for the α-diarylation of carbon nucleophiles to yield heavily functionalized quaternary products. Diaryliodonium salts are utilized to transfer both aryl groups under transition-metal-free conditions, which enables an atom-efficient and high-yielding method with broad functional group tolerance. The methodology is amenable to a wide variety of carbon nucleophiles and can be utilized in late-stage functionalization of complex arenes. Furthermore, it is co ...[more]

PMID: 39211612

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