1085-51-4Relevant articles and documents
Et2Zn-mediated stoichiometric C(sp)-H silylation of 1-alkynes and chlorosilanes
Huang, Pan,Xu, Dawen,Reich, Robert M.,Kaiser, Felix,Liu, Boping,Kühn, Fritz E.
, p. 1574 - 1577 (2019)
A first example of an Et2Zn mediated silylation of 1-aklynes is reported. A series of functional groups are tolerated in this reaction. Mechanistic studies support Zn alkynilides as intermediates in the reaction. This reaction protocol provides a practical method for the preparation of alkynylsilanes and expands the application of organometallic zinc in organic synthesis.
Alkylation of Terminal Alkynes under Zinc Lewis Acid Catalysis and Its Mechanistic Studies
Osano, Mana,Kida, Takeru,Yonekura, Kyohei,Tsuchimoto, Teruhisa
supporting information, p. 2825 - 2831 (2019/04/13)
With a zinc Lewis acid catalyst and proton sponge in toluene, terminal alkynes were found to undergo the alkylation by alkyl triflates to provide unsymmetrical internal alkynes. This is the first example that a simple alkyl chain other than benzylic and norbornyl units can be introduced onto the alkynyl carbon atom under Lewis acid catalysis. Mechanistic studies revealed that the activation of the alkyne by the zinc Lewis acid and proton sponge is the trigger of the reaction to give a monoalkynylzinc species, which successively reacts with the alkyl triflate to afford the internal alkyne. A radical pathway is unlikely in this system. (Figure presented.).
Single electron transfer-induced coupling of alkynylzinc reagents with aryl and alkenyl iodides
Okura, Keisho,Kawashima, Hitomi,Tamakuni, Fumiko,Nishida, Naoya,Shirakawa, Eiji
supporting information, p. 14019 - 14022 (2016/12/09)
Alkynylzinc reagents were found to undergo coupling with aryl and alkenyl iodides to give arylalkynes and alkenylalkynes without the aid of transition metals. The coupling reaction proceeds through a single electron transfer mechanism, where a substoichiometric amount of a phosphine works as an indispensable activator.
