Premium
Yne‐Allenes from 1‐Bromoallenes and Trimethylstannylacetylenes via Palladium‐Mediated C–C Coupling Reactions
Author(s) -
Saalfrank Rolf W.,
Haubner Martin,
Deutscher Christian,
Bauer Walter
Publication year - 1999
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/(sici)1099-0690(199909)1999:9<2367::aid-ejoc2367>3.0.co;2-9
Subject(s) - stille reaction , chemistry , palladium , orthoester , diastereomer , sigmatropic reaction , allene , conjugated system , stereochemistry , coupling reaction , organic chemistry , medicinal chemistry , catalysis , polymer
The Stille cross‐coupling of the bromoallenes 3 with the stannylalkynes 6 or distannylalkyne 8 provided a convenient route for the synthesis of the conjugated yne‐allenes 7 or the diastereomeric yne‐diallenes, meso ‐ 9 and ( R,R )/( S,S )‐ 9 . Analogously to 7 , the phosphorylyne‐allenes 14 were also prepared under Stille conditions, starting from the phosphorylallenes 12 and propargylstannane 6a . Alternatively, yne‐allenes 17 and 18 were obtained from hexadiynol 16 with orthoester 2b or diethoxychlorophosphane 13a by [3.3]‐ and [2.3]‐sigmatropic rearrangements.