Cyclobutene Formation by Borane Catalyzed [2+2] Cycloaddition of a Vinylphosphane with Conjugated Ynones

Dimesityl(vinyl)phosphane reacts with benzoyl(phenyl)acetylene under B(C6F5)3 catalysis to give the formal [2+2] cycloaddition product 1‐benzoyl‐2‐phenyl‐3‐dimesitylphosphinocyclobutene. Tris(pentafluorophenyl)borane catalyzed reactions of the bulky dimesityl(vinyl)phosphane with conjugated ynones y...

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Bibliographic Details
Published in:European journal of inorganic chemistry 2020-06, Vol.2020 (23), p.2270-2272
Main Authors: Tao, Xin, Gruber, Maurice M., Daniliuc, Constantin G., Mück‐Lichtenfeld, Christian, Kehr, Gerald, Erker, Gerhard
Format: Article
Language:English
Subjects:
Acetylene
Boron
Cycloaddition
Cyclobutenes
Homogeneous catalysis
Inorganic chemistry
Phosphorus
Ynones
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Summary:Dimesityl(vinyl)phosphane reacts with benzoyl(phenyl)acetylene under B(C6F5)3 catalysis to give the formal [2+2] cycloaddition product 1‐benzoyl‐2‐phenyl‐3‐dimesitylphosphinocyclobutene. Tris(pentafluorophenyl)borane catalyzed reactions of the bulky dimesityl(vinyl)phosphane with conjugated ynones yield cyclobutene derivatives. The reaction is probably initiated by phosphane attack at the activated carbon–carbon triple bond followed by ring‐closure and rearrangement to give the conjugated acyl‐cyclobutene products. Isomerization to the non‐conjugated isomer takes place during chromatography.
ISSN:1434-1948
1099-0682
DOI:10.1002/ejic.202000293