5111-41-1Relevant academic research and scientific papers
Direct Cross-Couplings of Propargylic Diols
Green, Nicholas J.,Willis, Anthony C.,Sherburn, Michael S.
supporting information, p. 9244 - 9248 (2016/08/05)
[Pd(PPh3)4] catalyzes a Suzuki–Miyaura-like twofold cross-coupling sequence between underivatized propargylic diols and either aryl or alkenyl boronic acids to furnish highly substituted 1,3-dienes. Thus, 2,3-diaryl-1,3-butadienes and their dialkenic congeners ([4]dendralenes) are delivered in a (pseudo)halogen-free, single-step synthesis which supersedes existing methods. Allenols are also readily formed. Treatment of these single- and twofold cross-coupled products with acid leads to remarkably short syntheses of highly-substituted benzofulvenes and aryl indenes, respectively.
Flash chemistry using trichlorovinyllithium: Switching the reaction pathways by high-resolution reaction time control
Nagaki, Aiichiro,Takahashi, Yusuke,Henseler, Andrea,Matsuo, Chika,Yoshida, Jun-Ichi
, p. 214 - 216 (2015/03/05)
High-resolution reaction time control in flow microreactors enables the reaction-pathway switching of trichlorovinyllithium generated by the H/Li exchange of trichloroethene. The method was successfully app lied to the synthesis of 1,1,2-trichloroalkenes,
Lithiation of 1,2-dichloroethene in flow microreactors: Versatile synthesis of alkenes and alkynes by precise residence-time control
Nagaki, Aiichiro,Matsuo, Chika,Kim, Songhee,Saito, Kodai,Miyazaki, Atsuo,Yoshida, Jun-Ichi
supporting information; experimental part, p. 3245 - 3248 (2012/05/31)
It′s all about the timing: Precise control of the residence time (tRx; see picture) of reactive intermediates in flow microreactors enables the reaction pathway of lithiated 1,2-dichloroethene to be switched to produce either alkenes or alkynes. This method also allows versatile syntheses of asymmetric disubstituted dichloroalkenes and alkynes. Copyright
Gold-Catalyzed stereocontrolled synthesis of 2,3-Bis(acetoxy)-1,3-dienes
Huang, Xiaogen,De Haro, Teresa,Nevado, Cristina
supporting information; experimental part, p. 5904 - 5908 (2010/03/03)
A 1,4-bis(propargyl acetates) undergo a highly selective tandem 1,2-/1,2-Bis(acetoxy) migration to give 2,3-Bis(acetoxy)-1,3-dienes, that, depending on the catalyst of choice,(1Z,3Z) or (1Z,3E and 1E,3Z)-1,3-dienes can be obtained in a stereocontrolled manner. It was found that the 1,2-Bis(acetoxy) migration was favored in all studied cases and no allene product was observed in the reaction mixtures. It was also found that more e sterically demanding substrate dramatically improved the selectivity thereby revealing the key role of sterics in the stereocontrol of these transformations. The results show that the choice of the acetoxy migrating first seemed to be of key importance and is determined both by the electronic character and sterical bulkiness of substituents at the propargylic position.
Ligand accelerated indium(III)-catalyzed asymmetric alkynylation of aldehydes with 2-methyl-3-butyn-2-ol as an ethyne equivalent donor
Harada, Shinji,Takita, Ryo,Ohshima, Takashi,Matsunaga, Shigeki,Shibasaki, Masakatsu
, p. 948 - 950 (2008/01/06)
Indium(III)-catalyzed asymmetric alkynylation of aryl, heteroaryl, alkyl and alkenyl aldehydes with 2-methyl-3-butyn-2-ol as an ethyne equivalent donor was realized, and products were obtained in moderate to good yields (up to 97%) and high enantioselecti
Regiocontrolled Formation of 4,5-Dihydro-3(2H)-furanones from 2-Butyne-1,4-diol Derivatives. Synthesis of Bullatenone and Geiparvarin
Saimoto, Hiroyuki,Hiyama, Tamejiro,Nozaki, Hitosi
, p. 3078 - 3087 (2007/10/02)
Two new methods for selective hydration of 1,1,4-trisubstituted 2-butyne-1,4-diols (1) to give 4,5-dihydro-3(2H)-furanone derivatives are reported.The first involves selective monoacetylation of the less hindered hydroxyl group of 1 followed by Ag(I)-cata
