64846-61-3Relevant academic research and scientific papers
In Situ Generation of Alkynylzinc and Its Subsequent Negishi Reaction in a Flow Reactor
Kandasamy, Mohanraj,Huang, Yu- Hsuan,Ganesan, Balaji,Senadi, Gopal Chandru,Lin, Wei-Yu
, p. 4349 - 4356 (2019/07/03)
A highly efficient and convenient Negishi cross-coupling reaction has been developed for the synthesis of unsymmetrical alkynes and enynes in a continuous-flow process. The reaction proceeds through an in situ generated alkynylzinc reagent by the reaction of lithium acetylide with zinc halide at room temperature followed by a cross-coupling reaction with aryl or vinyl iodides. The notable features of this work compared to the conventional benchtop method are mild reaction conditions, good to excellent yields, broad functional-group compatibility, short residence time (73 sec) and especially desilylation of TMS group with the residence time of only 10.5 sec.
Direct preparation of arylethynylzinc bromides and their application to cross-coupling reactions
Joo, Seong-Ryu,Kim, Jong-Sung,Kim, Seung-Hoi
, p. 3267 - 3270 (2017/07/27)
A novel synthetic protocol for the preparation of arylethynylzinc bromides has been developed. Thus-obtained organozinc reagents were successfully employed in the subsequent cross-coupling reactions with a broad range of aryl halides providing the corresponding alkynylated compounds in good to excellent yields.
Alkynylthioimidazolium Salts: Efficient Reagents for the Synthesis of Alkynyl Sulfides by Electrophilic Thioalkynylation
Pe?a, Javier,Talavera, Garazi,Waldecker, Bernd,Alcarazo, Manuel
supporting information, p. 75 - 78 (2017/01/09)
The efficient synthesis of a series of alkynylthioimidazolium salts through reaction of organozinc compounds with dibromo(imidazolium)sulfuranes is reported. Addition of Grignard reagents to these new species provided a highly modular, clean, and scalable access to a broad variety of alkynyl sulfides in good-to-excellent yields. The utility of this protocol was showcased by the preparation of alkynyl sulfides, which are particularly difficult to obtain or simply unavailable through the existing methodologies. In addition, the synthetic method was extended to the preparation of alkynyl selenides.
Synthesis of potentially biologically active 6-(1,3-butadiynyl)purines
K?ová?ek,Dvo?ák
, p. 40 - 47 (2015/01/30)
1,3-Alkadiynyl(trimethyl)silanes were prepared by the Negishi or Sonogashira reactions of bromoethynyl (trimethyl)silane with several terminal alkynes in 34-75% yield. However, the direct Hiyama coupling of these compounds with 6-iodopurine derivatives ha
Negishi cross-coupling reaction as a simple and efficient route to functionalized amino and alkoxy carbene complexes of chromium, molybdenum, and Tungsten
Tobrman, Tom,Jurskov, Ivana,Dvok, Dalimil
, p. 6593 - 6603 (2015/02/19)
Synthesis of functionalized phenyl, 2-thienyl, and N-methyl-pyrrol-2-yl Fischer carbene complexes of chromium and tungsten was achieved via a Negishi cross-coupling reaction of metalated aminocarbenes in the presence of a palladium catalyst. The reverse a
Zn(ii) chloride-catalyzed direct coupling of various alkynes with acetals: Facile and inexpensive access to functionalized propargyl ethers
Suzuki, Itaru,Yasuda, Makoto,Baba, Akio
, p. 11620 - 11622 (2013/12/04)
The coupling of acetals with various alkynes was achieved using only 1 mol% of inexpensive and mild Lewis acid ZnCl2, which furnished propargyl ethers. The coupling was catalyzed by Zn(OMe)Cl, which was generated in situ to form an alkynylzinc species. This protocol was allowed to expand to a one-pot subsequent reaction with allylchlorosilane to obtain a 1,4-enyne product.
