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Intramolecular trans ‐Carbocarbonation of Carbon‐Carbon Triple Bonds by an anti ‐Carbopalladation/Suzuki Coupling Cascade
Author(s) -
Reding Andreas,
Ohta Naoki,
Sebrantke Philip,
Jones Peter G.,
Nakao Yoshiaki,
Werz Daniel B.
Publication year - 2020
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.202000545
Subject(s) - intramolecular force , triple bond , alkyne , chemistry , suzuki reaction , ring (chemistry) , cascade , double bond , reinforced carbon–carbon , hydride , palladium , stereochemistry , medicinal chemistry , catalysis , organic chemistry , materials science , metal , chromatography , composite number , composite material
An intramolecular palladium‐catalyzed trans ‐carbocarbonation cascade is presented that consists of a formal anti ‐carbopalladation of an internal carbon‐carbon triple bond terminated by a Suzuki cross‐coupling reaction. The key to success in obtaining the anti ‐geometry of the emerging double bond is the use of alkyne units with substituents that avoid β ‐hydride elimination (e. g. tert‐ butyl or silyl). The products, involving tetrasubstituted double bonds embedded in a seven‐ or eight‐membered ring system, are formed in moderate to good yields.