40596-19-8Relevant academic research and scientific papers
Versatile Homoallylic Boronates by Chemo-, SN2′-, Diastereo- and Enantioselective Catalytic Sequence of Cu?H Addition to Vinyl-B(pin)/Allylic Substitution
Lee, Jaehee,Torker, Sebastian,Hoveyda, Amir H.
, p. 821 - 826 (2017)
A highly chemo-, diastereo- and enantioselective catalytic method that efficiently combines a silyl hydride, vinyl-B(pin) (pin=pinacolato) and (E)-1,2-disubstituted allylic phosphates is introduced. Reactions, best promoted by a Cu-based complex with a chiral sulfonate-containing N-heterocyclic carbene, are broadly applicable. Aryl-, heteroaryl-, alkenyl-, alkynyl- and alkyl-substituted allylic phosphates may thus be converted to the corresponding homoallylic boronates and then alcohols (after C?B bond oxidation) in 46–91 % yield and in up to >98 % SN2′:SN2 ratio, 96:4 diastereomeric ratio and 98:2 enantiomeric ratio. The reasons why an NHC?Cu catalyst is uniquely effective (vs. the corresponding phosphine systems) and the basis for different trends in stereoselectivity are provided with the aid of DFT calculations.
Method for preparing alcohol through reaction of Suzuki no exogenous alkali (by machine translation)
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Paragraph 0022-0026; 0042-0044, (2020/02/14)
The method for synthesizing the alcohol compound by. using the method disclosed by the invention for preparing .the alcohol compound by adopting the method Suzuki disclosed by the invention has the advantages that the reaction system, is convenient and convenient, to prepare, and the reaction system is convenient to prepare . Suzuki. (by machine translation)
Efficient hydroarylation of terminal alkynes with sodium tetraphenylborate performed in water under mild conditions
Koci?cka,Trzeciak
, (2019/11/02)
The hydroarylation of terminal alkynes with sodium tetraphenylborate was performed in high yield within 3 h at room temperature in water, using palladium(II) complexes with imidazole ligands as catalysts. Under these conditions, differently substituted phenylacetylene substrates were converted to arylalkenes and aryl-substituted dienes. High conversion and excellent selectivity were achieved in the hydroarylation of alkynols with sodium tetraphenylborate. Only one product, arylalkene with an OH group, was formed in these reactions with the yield dependent on the kind of alkynol used. A plausible hydroarylation reaction mechanism was proposed on the basis of the palladium species identified in the reaction mixture and H/D exchange studies. The contribution of water as the hydride source was evidenced.
Cross-coupling reaction of allylic ethers with aryl Grignard reagents catalyzed by a nickel pincer complex
Hashimoto, Toru,Funatsu, Kei,Ohtani, Atsufumi,Asano, Erika,Yamaguchi, Yoshitaka
, (2019/07/10)
A cross-coupling reaction of allylic aryl ethers with arylmagnesium reagents was investigated using β-aminoketonato- and β-diketiminato-based pincer-type nickel(II) complexes as catalysts. An β-aminoketonato nickel(II) complex bearing a diphenylphosphino group as a third donor effectively catalyzed the reaction to afford the target cross-coupled products, allylbenzene derivatives, in high yield. The regioselective reaction of a variety of substituted cinnamyl ethers proceeded to give the corresponding linear products. In contrast, α- and γ-alkyl substituted allylic ethers afforded a mixture of the linear and branched products. These results indicated that the coupling reaction proceeded via a π-allyl nickel intermediate.
