196599-47-0Relevant academic research and scientific papers
Selective Hydroarylation of 1,3-Diynes Using a Dimeric Manganese Catalyst: Modular Synthesis of Z-Enynes
Yan, Zhongfei,Yuan, Xiang-Ai,Zhao, Yue,Zhu, Chengjian,Xie, Jin
supporting information, p. 12906 - 12910 (2018/09/25)
The transition-metal-catalyzed selective hydroarylation of unsymmetrical alkynes represents the state-of-art in organic chemistry, and still mainly relies on the use of precious late-transition-metal catalysts. Reported herein is an unprecedented MnI-catalyzed hydroarylation of unsymmetrical 1,3-diyne alcohols with commercially available arylboronic acids with predictive selectivity. This method addresses the challenges in regio-, stereo-, and chemoselectivity. It offers a general, convenient and practical strategy for the modular synthesis of multisubstituted Z-configurated conjugated enynes. This protocol is distinguished by its operational simplicity, complete selectivity, excellent functional-group compatibility, and gram-scale potential. A dimeric MnI species, Mn2(CO)8Br2, was proven to be a much more efficient catalyst precursor than Mn(CO)5Br.
Glaser-Hay hetero-coupling in a bimetallic regime: A Ni(II)/Ag(i) assisted base, ligand and additive free route to selective unsymmetrical 1,3-diynes
Mohanty, Anuradha,Roy, Sujit
supporting information, p. 10796 - 10799 (2017/10/06)
A Ni(OAc)2/Ag(OTf) catalysed coupling of aryl alkynes and propargylic alcohol/ether/ester gave the corresponding unsymmetrical 1,3-diynes in good to excellent yields. The reaction does not require bases, ligands or additives and shows excellent hetero-selectivity, thereby addressing the current challenges in the field of coupling of two different terminal alkynes.
Homo and heterocoupling of terminal alkynes using catalytic CuCl 2 and DBU
Balamurugan, Rengarajan,Naveen, Naganaboina,Manojveer, Seetharaman,Nama, Masthan Vali
experimental part, p. 567 - 575 (2012/01/02)
Homocoupling of terminal alkynes has been efficiently achieved using catalytic amounts of CuCl2 and DBU. This methodology could be extended to couple two different terminal alkynes together by taking one of the alkyne partners, preferably the electron rich alkyne, in five fold excess than the other. CSIRO 2011.
A strictly "pair"-selective synthesis of conjugated diynes via Pd-catalyzed cross coupling of 1,3-diynylzincs: A superior alternative to the Cadiot-Chodkiewicz reaction
Negishi, Ei-Ichi,Hata, Mitsuhiro,Xu, Caiding
, p. 3687 - 3689 (2007/10/03)
(matrix presented) A strictly "pair"-selective synthesis of conjugated diynes via Pd-catalyzed cross coupling of 1,3-diynylzincs is described. This method, like the Cadiot-Chodkiewicz reaction, requires three steps for the synthesis of R1C≡CC≡CR2 from R1C≡CH, R2X, and HC≡CH. However, the high "pair"-selectivity permitting high-yield production of the desired conjugated diynes without separation of symmetrical diynes promises to make the present protocol superior to the Cadiot-Chodkiewicz reaction in many cases.
