920282-76-4Relevant academic research and scientific papers
Transition metal-free coupling of terminal alkynes and hypervalent iodine-based alkyne-transfer reagents to access unsymmetrical 1,3-diynes
Sch?rgenhumer,Waser
, p. 7561 - 7563 (2018/11/02)
A variety of unsymmetrical 1,3-diynes can easily be accessed in good yields under catalyst- and transition metal-free conditions by reacting terminal alkynes with hypervalent iodine-based electrophilic alkyne-transfer reagents.
Gold-Catalyzed Oxidative Coupling of Alkynes toward the Synthesis of Cyclic Conjugated Diynes
Ye, Xiaohan,Peng, Haihui,Wei, Chiyu,Yuan, Teng,Wojtas, Lukasz,Shi, Xiaodong
supporting information, p. 1983 - 1993 (2018/10/02)
Gold-catalyzed oxidative coupling of alkynes was developed as an efficient approach for the synthesis of challenging cyclic conjugated diynes (CCD). Compared with the classic copper-promoted oxidative coupling reaction of alkynes, this gold-catalyzed process exhibited a faster reaction rate due to rapid reductive elimination from the Au(III) intermediate. This unique reactivity thus allowed a challenging diyne macrocyclization to take place with high efficiency. Condition screening revealed an [(n-Bu)4N]+[Cl-Au-Cl]? salt as the optimal pre-catalyst. Macrocycles with ring size between 13 and 28 atoms were prepared in moderate to good yields, which highlighted the broad substrate scope of this new strategy. Furthermore, the synthetic utilities of the CCDs for copper-free click chemistry have been demonstrated, showcasing the potential application of this strategy in biological systems. Macrocycles are important structural moieties in medicinal and biological research, and efficient methods for macrocyclization are always in high demand. With the unique conformation having six carbon atoms in a linear geometry, the cyclic conjugated diynes (CCD) present greater synthetic challenges and have been much less explored. Therefore, application of these unique macrocycles in biological studies is largely unexplored. Here, we describe the discovery of gold-catalyzed Glaser-Hay type oxidative coupling of terminal alkynes to achieve CCD under diluted conditions with broad substrate scope and great functional group compatibility. Taking advantage of the 14-member cyclic diyne, a copper-free click chemistry was achieved, which provided an effective alternative strategy for the traditional cyclooctyne-based azide-alkyne cycloaddition, suggesting a promising future for this method in tackling challenging problems in related biological and medicinal research. Gold-catalyzed oxidative coupling of alkynes was developed as an efficient approach for the synthesis of challenging cyclic conjugated diyne. Compared with copper-promoted oxidative coupling, this protocol allowed macrocyclization under dilute conditions with good overall reactivity and high functional group tolerance. The success in achieving copper-free click chemistry on cyclic conjugated diyne highlights its potential application in biological and medicinal research.
Exploiting the dual role of ethynylbenziodoxolones in gold-catalyzed C(sp)-C(sp) cross-coupling reactions
Banerjee, Somsuvra,Patil, Nitin T.
supporting information, p. 7937 - 7940 (2017/07/22)
Reported herein is the gold-catalyzed alkynylation of terminal alkynes using ethynylbenziodoxolones (EBXs), where EBXs serve a dual role as oxidants as well as alkyne transfer agents to access unsymmetrical 1,3-diynes. Hence, the catalytic system requires no external oxidants and is compatible with a broad range of substrates, including those with polar functional groups such as NH, OH and B(OH)2.
Gold-catalyzed oxidative cross-coupling of terminal alkynes: Selective synthesis of unsymmetrical 1,3-diynes
Peng, Haihui,Xi, Yumeng,Ronaghi, Nima,Dong, Boliang,Akhmedov, Novruz G.,Shi, Xiaodong
supporting information, p. 13174 - 13177 (2015/03/30)
Gold-catalyzed oxidative cross-coupling of alkynes to unsymmetrical diynes has been achieved for the first time. A N,N-ligand (1,10-Phen) and PhI(OAc)2 were identified as crucial factors to promote this transformation, giving the desired cross-
Regioselective trapping of terminal di-, tri-, and tetraynes with benzyl azide
Luu, Thanh,McDonald, Robert,Tykwinski, Rik R.
, p. 6035 - 6038 (2007/10/03)
(Chemical Equation Presented) The reaction of benzyl azide with terminal di-, tri-, and tetraynes appended with a range of functional groups has been explored. Standard reaction conditions for BnN3 catalyzed by CuSO4·5H2O
