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Lewis Basic Salt-Promoted Organosilane Coupling Reactions with Aromatic Electrophiles.

ABSTRACT: Lewis basic salts promote benzyltrimethylsilane coupling with (hetero)aryl nitriles, sulfones, and chlorides as a new route to 1,1-diarylalkanes. This method combines the substrate modularity and selectivity characteristic of cross-coupling with the practicality of a base-promoted protocol. In addition, a Lewis base strategy enables a complementary scope to existing methods, employs stable and easily prepared organosilanes, and achieves selective arylation in the presence of acidic functional groups. The utility of this method is demonstrated by the synthesis of pharmaceutical analogues and its use in multicomponent reactions.

SUBMITTER: Reidl TW

PROVIDER: S-EPMC8510683 | biostudies-literature | 2021 Aug

REPOSITORIES: biostudies-literature

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Lewis Basic Salt-Promoted Organosilane Coupling Reactions with Aromatic Electrophiles.

Reidl Tyler W TW Bandar Jeffrey S JS

Journal of the American Chemical Society 20210727 31

Lewis basic salts promote benzyltrimethylsilane coupling with (hetero)aryl nitriles, sulfones, and chlorides as a new route to 1,1-diarylalkanes. This method combines the substrate modularity and selectivity characteristic of cross-coupling with the practicality of a base-promoted protocol. In addition, a Lewis base strategy enables a complementary scope to existing methods, employs stable and easily prepared organosilanes, and achieves selective arylation in the presence of acidic functional gr ...[more]

PMID: 34314159

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