1095091-93-2Relevant academic research and scientific papers
Sulfonamidoquinoline/palladium(II)-dimer complex as a catalyst precursor for palladium-catalyzed γ-Selective and stereospecific allyl-aryl coupling reaction between allylic acetates and arylboronic acids
Makida, Yusuke,Ohmiya, Hirohisa,Sawamura, Masaya
supporting information; experimental part, p. 410 - 414 (2011/10/03)
On neutral territory: A neutral palladium(II)-dimer catalyst system incorporating anionic sulfonamidoquinoline ligands is effective for the γ-selective and stereospecific allyl-aryl coupling between acyclic (E)-allylic acetates and arylboronic acids. Copy
Copper-catalyzed γ-selective and stereospecific allyl-aryl coupling between (Z)-acyclic and cyclic allylic phosphates and arylboronates
Ohmiya, Hirohisa,Yokokawa, Natsumi,Sawamura, Masaya
supporting information; experimental part, p. 2438 - 2440 (2010/07/10)
A Cu-catalyzed allyl-aryl coupling reaction between (Z)-acyclic or cyclic allylic phosphates and arylboronates proceeds with excellent γ-E-selectivity and 1,3-anti chirality transfer, which gives the corresponding coupling products with benzylic and allylic stereogenic centers. The wide availability and easy-to-handle nature of arylboronates, the inexpensiveness of the Cu catalyst system, and the high regio- and stereoselectivities are attractive features of this protocol.
Palladium-catalyzed γ-selective and stereospecific allyl-aryl coupling between acyclic allylic esters and arylboronic acids
Ohmiya, Hirohisa,Makida, Yusuke,Li, Dong,Tanabe, Masahito,Sawamura, Masaya
supporting information; experimental part, p. 879 - 889 (2010/03/25)
Reactions between acyclic (E)-allylic acetates and arylboronic acids in the presence of a palladium catalyst prepared from Pd(OAc)2, phenanthroline (or bipyridine), and AgSbF6 (1:1.2:1) proceeded with excellent γ-selectivity to afford allyl-aryl coupling products with E-configuration. The reactions of α-chiral allylic acetates took place with excellent α-to-γ chirality transfer with syn stereochemistry to give allylated arenes with a stereogenic center at the benzylic position. The reaction tolerated a broad range of functional groups in both the allylic acetates and the arylboronic acids. Furthermore, γ-arylation of cinnamyl alcohol derivatives afforded gem-diarylalkane derivatives containing an unconjugated alkenic substituent. The synthetic utility of this method was demonstrated by its utilization in an efficient synthesis of (+)-sertraline, an antidepressant agent. The observed γ-regioselectivity and E-1,3-syn stereochemistry were rationalized based on a Pd(II) mechanism involving transmetalation between a cationic mono(acyloxo)palladium(II) complex and arylboronic acid, and directed carbopalladation followed by syn-β-acyloxy elimination. The results of stoichiometric reactions of palladium complexes related to possible intermediates were fully consistent with the proposed mechanism.
