108946-36-7Relevant academic research and scientific papers
Organoborane-catalyzed selective 1,2-reduction of alkynones with hydride transfer: Synthesis of benzyl alkynes
Li, Huilin,Man, Qinghong,Ren, Yangqing,She, Xuegong,Wang, Lei,Yang, Mingyu,Yang, Zhigang,Zhai, Lele
supporting information, (2022/01/28)
Benzyl alkynes are important organic building blocks in organic synthesis. We report herein a B(C6F5)3-catalyzed site-selective 1,2-reduction of readily available alkynones to access benzyl alkyne derivatives. Under the de
Visible Light-Induced Reductive Alkynylation of Aldehydes by Umpolung Approach
Tanaka, Ibuki,Sawamura, Masaya,Shimizu, Yohei
supporting information, p. 520 - 524 (2022/01/20)
Reductive alkynylation of aldehydes by the Umpolung approach was developed using a photoredox catalyst under blue LED irradiation. Ketyl radicals, generated by single-electron reduction of aldehydes through proton-coupled electron transfer (PCET), reacted with electrophilic alkynylsulfones. Sterically demanding bulky aldehydes reacted smoothly under the Umpolung reaction conditions. Moreover, the alkynylation proceeded chemoselectively with an aryl aldehyde group in the presence of other carbonyl groups including an aliphatic aldehyde group.
Ti-catalyzed regioselective ring-opening alkynylation of epoxides with haloalkynes
Zhang, Di,Li, Hao,Yi, Dong,Tu, Shijing,Qi, Zhongyu,Wei, Siping,Fu, Qiang,Fu, Haiyan,Du, Xi
supporting information, (2021/11/01)
Ti-catalyzed ring-opening alkynylation of epoxides with haloalkynes has been achieved, allowing an efficient and regioselective entry to various propargylic alcohols in moderate to good yields. The developed protocol features extremely mild reaction conditions, broad substrate scope, varied functional group compatibility, and chemospecificity in the rearrangements of epoxides to aldehydes.
A mild and efficient AgSbF6-catalyzed synthesis of fully substituted pyrroles through a sequential propargylation/amination/ cycloisomerization reaction
Gujarathi, Satheesh,Liu, Xingui,Song, Lin,Hendrickson, Howard,Zheng, Guangrong
, p. 5267 - 5273 (2014/07/08)
Development of an efficient synthesis of fully substituted pyrroles via a sequential propargylation/amination/cycloisomerization was accomplished using AgSbF6 as a catalyst. The one-pot three-component reaction of propargylic alcohols, 1,3-dica
A mild and efficient AgSbF6-catalyzed synthesis of fully substituted pyrroles through a sequential propargylation/amination/cycloisomerization reaction
Gujarathi, Satheesh,Liu, Xingui,Song, Lin,Hendrickson, Howard,Zheng, Guangrong
, p. 5267 - 5273 (2014/12/10)
Development of an efficient synthesis of fully substituted pyrroles via a sequential propargylation/amination/cycloisomerization was accomplished using AgSbF6as a catalyst. The one-pot three-component reaction of propargylic alcohols, 1,3-dicar
A convenient approach to β-heteroarylated (C-N bond) ketones from Cs2CO3 promoted reaction between propargyl alcohols and nitrogen-heterocycles
Bhanuchandra,Kuram, Malleswara Rao,Sahoo, Akhila K.
experimental part, p. 3538 - 3555 (2012/05/20)
An efficient and direct approach to β-heteroarylated (C-N bond) ketones is demonstrated. Base promoted redox isomerization of propargyl alcohol to α,β-unsaturated ketone followed by conjugate addition to NH-heteroarenes affords a wide range of β-heteroarylated ketones in good to excellent yields. Aryl, heteroaryl, alkyl C(sp), and terminal alkynes containing unactivated propargyl alcohols effectively undergo redox-isomerization conjugate addition (RICA) with NH-heteroarenes. Reaction of 3-substituted pyrazoles or indazole with propargyl alcohols enables highly regioselective products. A diverse range of NH-bearing nucleophiles such as: pyrazoles, imidazole, triazoles, pyrrole, indoles and aniline participate in this reaction and deliver the corresponding β-heteroarylated ketones.
Tandem amination/cycloisomerization of aryl propargylic alcohols with 2-aminopyridines as an expedient route to imidazo[1,2-a]pyridines
Liu, Ping,Deng, Chun-Lin,Lei, Xinsheng,Lin, Guo-Qiang
experimental part, p. 7308 - 7316 (2012/01/06)
A new tandem route leading to imidazo[1,2-a]pyridines has been explored through the direct amination of aryl propargylic alcohols with 2-aminopyridines and their subsequent intramolecular cycloisomerization. A ZnCl2/CuCl system has been develop
Solvent-free synthesis of propargylic alcohols using zno as a new and reusable catalyst by direct addition of alkynes to aldehydes
Hosseini-Sarvari, Mona,Mardaneh, Zahra
experimental part, p. 4297 - 4303 (2012/02/16)
Under solvent-free conditions, the synthesis of propargylic alcohols by direct addition of terminal alkynes to aldehydes promoted by ZnO as a novel, commercially, and cheap catalyst is described. Furthermore, the catalyst can be reused for several times w
Synthesis of phosphine-ligated zinc acetylide dimers: Enhanced reactivity in carbonyl additions
Wilson, Erin E.,Oliver, Allen G.,Hughes, Russell P.,Ashfeld, Brandon L.
experimental part, p. 5214 - 5221 (2011/11/13)
Phosphine-ligated dinuclear zinc acetylides effectively promote the alkynylation of carbonyl derivatives. Good to excellent yields (46-91%) of the corresponding propargylic alcohols were obtained from a wide range of substrates. Crystallographic evidence
Chemoselective addition of in situ prepared lithium alkynyl borates to aldehydes: a practical and transition metal free approach toward the synthesis of propargylic alcohols
Francesco, Irene Notar,Renier, Antoine,Wagner, Alain,Colobert, Fran?oise
experimental part, p. 1386 - 1389 (2010/04/25)
A convenient synthesis of functionalized propargylic alcohols arising from the 1,2-addition of lithium alkynyl-trimethyl borate onto aldehydes under transition metal free mild conditions is reported. The reaction tolerates a wide range of functional groups, is highly chemoselective and the propargylic alcohols are isolated in good to excellent yields.
