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Tris(pentafluorophenyl)borane‐Catalyzed Reaction of Phosphorus/Boron and Nitrogen/Boron Frustrated Lewis Pair Dihydrogen Activation Products with Alkenes and Alkynes
Author(s) -
Wang Tongdao,
Jentgens Xenia,
Daniliuc Constantin G.,
Kehr Gerald,
Erker Gerhard
Publication year - 2017
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201601229
Subject(s) - chemistry , borane , medicinal chemistry , phenylacetylene , frustrated lewis pair , catalysis , alkene , hydride , boron , boranes , alkyne , regioselectivity , lewis acids and bases , organic chemistry , hydrogen
The N/B frustrated Lewis pair (FLP) dihydrogen splitting product 10 undergoes a facile B(C 6 F 5 ) 3 ‐catalyzed regioselective trans ‐1,2‐hydridoborate addition reaction to phenylacetylene to give the cis ‐styryl‐containing ammonium/borate zwitterion 12 . The B(C 6 F 5 ) 3 ‐catalyzed reaction of 10 with 1‐phenylpropyne proceeded analogously to give 13 . The respective [B]/H − addition to styrene gave the corresponding [B]−CH 2 CH 2 Ph‐containing product 14 under mild conditions. We obtained evidence that the reaction is initiated by hydride migration between the two B centers involved and is then continued by hydride addition to the borane activated alkyne or alkene, respectively. The H 2 ‐splitting product 4 derived from the ethylene‐bridged P/B FLP 3 reacted analogously with these alkynes and also with styrene under B(C 6 F 5 ) 3 catalysis to yield the respective alkenyl‐ or alkyl borate products. The new addition products were characterized by using XRD.