180071-98-1Relevant articles and documents
First Examples of Transition-Metal Free Sonogashira-Type Couplings
Leadbeater, Nicholas E.,Marco, Maria,Tominack, Bonnie J.
, p. 3919 - 3922 (2003)
(Matrix presented) We report here our observation that, using appropriate reaction conditions, the Sonogashira reaction can be performed without the need for transition-metal catalysts. Our approach involves the use of water as a solvent, poly(ethylene glycol) as a phase-transfer agent, and sodium hydroxide as a base. The methodology works, to differing extents, for aryl iodides and bromides.
Diorganyl tellurides as substrates in Sonogashira coupling reactions under mild conditions
Zhang, Shaozhong,Ailneni, Chandra,Al-Mohammed Baqer, Osamah,Lolla, Mahati,Mannava, Bala Bharathi,Siraswal, Parvinlal,Yen, Changchi,Jin, Jin
supporting information, p. 217 - 225 (2019/11/22)
A new method of Sonogashira coupling reactions between diorganyl tellurides and terminal alkynes is reported. The coupling reactions are performed using Pd(dppf)Cl2 as a catalyst, CuI as a co-catalyst in the presence of K2CO3 in DMSO. The reactions are carried out at room temperature and completed within 2 h when phenyl acetylene is used as a terminal alkyne. For aliphatic terminal alkynes, such as 1-hexyne and 1-octyne, an elevated temperature and longer reaction time are needed for the completion of the reactions. This process results in good yields of Sonogashira coupling products which is applicable for diaryl, divinyl and dialkynyl tellurides but not applicable for dialkyl tellurides.
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.