60214-15-5Relevant academic research and scientific papers
Rh(III)-Catalyzed [3 + 2] Spirocyclization of 2 H-Imidazoles with 1,3-Diynes for the Synthesis of Spiro-[imidazole-indene] Derivatives
Luo, Yi,Liu, Hao,Zhang, Jing,Liu, Man,Dong, Lin
supporting information, p. 7604 - 7608 (2020/10/09)
An effective strategy to synthesize spirocyclic compounds, [imidazole-4,1′-indene], has been efficaciously developed relied on Rh(III)-catalyzed [3 + 2] spirocyclization of 2H-imidazoles and 1,3-diynes with excellent chemselectivity and regioselectivity.
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.
Application of the Solid-Supported Glaser-Hay Reaction to Natural Product Synthesis
Lampkowski, Jessica S.,Uthappa, Diya M.,Halonski, John F.,Maza, Johnathan C.,Young, Douglas D.
, p. 12520 - 12524 (2016/12/23)
The Glaser-Hay coupling of terminal alkynes is a useful synthetic reaction for the preparation of polyynes; however, chemoselectivity issues have precluded its widespread utilization. Conducting the reaction on a solid-support provides a mechanism to alle
Preparation of asymmetrical polyynes by a solid-supported Glaser-Hay reaction
Lampkowski, Jessica S.,Durham, Corinn E.,Padilla, Marshall S.,Young, Douglas D.
supporting information, p. 424 - 427 (2015/02/05)
Polyynes exhibit both unique photophysical properties and biological activities, necessitating efficient syntheses towards these core structures. A novel methodology for the construction of highly conjugated asymmetrical polyynes has been developed in a chemoselective fashion utilizing a solid-support. The synthesis has been applied to prepare a small library of polyynes in good to moderate yield. Moreover, their interesting fluorescence properties have been investigated, demonstrating the ability to tune fluorescence through selection of appropriate synthetic building blocks. This journal is
One-pot formation and derivatization of di- and triynes based on the Fritsch-Buttenberg-Wiechell rearrangement
Luu, Thanh,Morisaki, Yasuhiro,Cunningham, Nina,Tykwinski, Rik R.
, p. 9622 - 9629 (2008/03/15)
(Chemical Equation Presented) A divergent, one-pot synthesis of functionalized polyynes has been developed. Beginning with the appropriately substituted dibromoolefinic precursor, a carbenoid Fritsch-Buttenberg-Wiechell (FBW) rearrangement is used to gene
Highly efficient and selective synthesis of conjugated triynes and higher oligoynes of biological and materials chemical interest via palladium-catalyzed alkynyl-alkenyl coupling
Metay, Estelle,Hu, Qian,Negishi, Ei-Ichi
, p. 5773 - 5776 (2007/10/03)
(Diagram presented) Iteration of a Pd-catalyzed reaction of alkynyl- and oligoynylzincs with (E)-ICH=CHCl followed by metalation-termination with electrophiles(E) has provided a linear route to conjugated tri- and tetraynes, and Pd-catalyzed monoalkynylation of 1,1-dibromoenynes accompanied by dehydrobromination has provided a convergent route to conjugated tri-, tetra-, and pentaynes. Both display unprecedented high efficiency and selectivity.
A one-pot synthesis and functionalization of polyynes
Morisaki, Yasuhiro,Luu, Thanh,Tykwinski, Rik R.
, p. 689 - 692 (2007/10/03)
A one-pot synthesis and derivatization of diynes and triynes is reported. The polyyne framework is formed from a dibromoolefin precursor based on a carbenoid rearrangement, and the resulting Li-acetylide is then trapped in situ with an electrophile to pro
A divergent synthesis of triyne natural products and glycosylated analogues using a carbenoid rearrangement
Luu, Thanh,Shi, Wei,Lowary, Todd L.,Tykwinski, Rik R.
, p. 3167 - 3178 (2007/10/03)
Using a carbenoid rearrangement to introduce the conjugated acetylenic framework, a series of triynols has been synthesized in five steps from 1,4-butynediol. Several of the triyne alcohols are known natural products and others are glycosylated analogues.
