Open AccessLewis Basic Salt-Promoted Organosilane Coupling Reactions with Aromatic Electrophiles
Author(s) -
Tyler W. Reidl,
Jeffrey S. Bandar
Publication year - 2021
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.1c05764
Subject(s) - chemistry , lewis acids and bases , electrophile , salt (chemistry) , aryl , combinatorial chemistry , substrate (aquarium) , selectivity , base (topology) , modularity (biology) , scope (computer science) , coupling (piping) , organic chemistry , catalysis , alkyl , programming language , mechanical engineering , mathematical analysis , oceanography , mathematics , biology , computer science , engineering , genetics , geology
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.