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Novel, Stereoselective and Stereospecific Synthesis of Allenylphosphonates and Related Compounds via Palladium‐Catalyzed Propargylic Substitution
Author(s) -
Kalek Marcin,
Stawinski Jacek
Publication year - 2011
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100119
Subject(s) - chemistry , stereospecificity , stereoselectivity , palladium , moiety , phosphonate , phosphinate , catalysis , substitution reaction , substitution (logic) , stereochemistry , combinatorial chemistry , organic chemistry , fire retardant , computer science , programming language
We have developed a novel method for the synthesis of allenylphosphonates and related compounds based on a palladium(0)‐catalyzed reaction of propargylic derivatives with H‐phosphonate, H‐phosphonothioate, H‐phosphonoselenoate, and H‐phosphinate esters. The reaction is stereoselective and stereospecific, and provides a convenient entry to a vast array of allenylphosphonates and their analogues with diverse substitution patterns in the allenic moiety and at the phosphorus center. Some mechanistic aspects of this new reaction were also investigated.