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Synthesis of a Chiral Borate Counteranion, Its Trityl Salt, and Application Thereof in Lewis‐Acid Catalysis
Author(s) -
Pommerening Phillip,
Mohr Jens,
Friebel Jonas,
Oestreich Martin
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700239
Subject(s) - chemistry , electrophile , lewis acids and bases , aldol reaction , boron , cationic polymerization , medicinal chemistry , catalysis , carbocation , salt (chemistry) , lithium (medication) , lewis acid catalysis , hydride , silicon , asymmetric induction , derivative (finance) , fluorine , carbon atom , polymer chemistry , organic chemistry , enantioselective synthesis , ring (chemistry) , medicine , hydrogen , financial economics , economics , endocrinology
The preparation of a chiral derivative of [B(C 6 F 5 ) 4 ] – in which the fluorine atom in the para position of each of the C 6 F 5 groups is replaced by a 1,1′‐binaphthalen‐2‐yl group is described. The new counteranion was isolated as its lithium, sodium, and trityl salts. The chiral trityl salt was then used as a catalyst in selected counteranion‐directed Diels–Alder reactions and a Mukaiyama aldol addition, but no asymmetric induction was achieved. Application of the chiral trityl salt to the generation of silicon cations by silicon‐to‐carbon hydride transfer from hydrosilanes failed, presumably as a result of the incompatibility of the relatively electron‐rich naphthyl groups in the borate and the cationic silicon electrophiles.