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Halogen‐Bonding‐Donor Catalyzed Cyanosilylation of Aldehydes
Author(s) -
Ueyama Kyohei,
Hayakawa Shunsuke,
Nishio Kazuhiro,
Sawaguchi Daiki,
Niitsuma Kenta,
Michii Shota,
Tsuruoka Ryoto,
Ozawa Miyuki,
Torita Koki,
Morita Yoshitsugu,
Komatsu Teruyuki,
Haraguchi Ryosuke,
Fukuzawa Shinichi
Publication year - 2021
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202100184
Subject(s) - chemistry , chemoselectivity , electrophile , halogen bond , lewis acids and bases , catalysis , cationic polymerization , halogen , substrate (aquarium) , combinatorial chemistry , polymer chemistry , organic chemistry , alkyl , oceanography , geology
Although halogen‐bonding has been utilized as an emerging means for activation of substrates, the use of the interaction for activation of relatively low Lewis basic electrophiles such as carbonyl compounds is still limited. Herein, we developed the halogen‐bonding‐donor donor catalyzed cyanosilylation of aldehydes via a synergistic activation mechanism, which were supported by a combined computational and experimental approach. The substrate scope for the reaction and the chemoselectivity of cationic XB‐donors are described.