108946-35-6Relevant academic research and scientific papers
Rhodium-Catalyzed Intermolecular trans-Disilylation of Alkynones with Unactivated Disilanes
He, Tao,Liu, Li-Chuan,Guo, Le,Li, Bin,Zhang, Qing-Wei,He, Wei
, p. 10868 - 10872 (2018)
Disilylation of alkynes could provide rapid entry to synthetically useful 1,2-bissilyl-alkenes, but is currently limited to activated disilanes reacting in an intramolecular fashion. Reported herein is an efficient rhodium(I)-catalyzed intermolecular disi
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.
Enantioselective Alkynylation of Aromatic Aldehydes Catalyzed by a Sterically Highly Demanding Chiral-at-Rhodium Lewis Acid
Luo, Shipeng,Zhang, Xiao,Zheng, Yu,Harms, Klaus,Zhang, Lilu,Meggers, Eric
, p. 8995 - 9005 (2017/09/11)
The enantioselective catalytic alkynylation of aromatic aldehydes is reported using a sterically highly hindered bis-cyclometalated rhodium-based Lewis acid catalyst featuring the octahedral metal as the only stereogenic center. Yields of 58-98% with 79-9
Enantioselective alkynylation of aldehydes with 1-haloalkynes catalyzed by tethered bis(8-quinolinato) chromium complex
Usanov, Dmitry L.,Yamamoto, Hisashi
, p. 1286 - 1289 (2011/04/16)
The first example of Cr-catalyzed asymmetric alkynylation of aldehydes with 1-iodo- and 1-bromoalkynes was developed. The use of tethered bis(8-quinolinato) chromium catalyst (3 mol %) allowed preparation of enantioenriched propargyl alcohols with good yields and enantioselectivities up to 92% ee. 1-Bromoalkynes can be activated by the introduction of a cobalt porphine cocatalyst, which enables shorter reaction times without any loss of enantiocontrol.
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
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
On the Chemistry of Acetylenic Titanium Compounds
Krause, Norbert,Seebach, Dieter
, p. 1845 - 1852 (2007/10/02)
Solutions of acetylenic titanium compounds of the type R-CC-Ti(OiPr)3 (5) were prepared in the usual way, and their reactions with various electrophiles were studied.The addition to aldehydes takes place at low temperature; however, for ketones, long reaction times at 0 deg C are necessary.Therefore a complete differentiation between these two functional groups can be achieved.In contrast to alkyl titanium compounds, the alkinyl derivatives are more basic than the corresponding lithium compounds.The use of reagents 5 instead of lithium acetylides does not result in a striking improvement of the diastereoselectivity of addition to chiral aldehydes.The phenyl-substituted reagent (5, R = C6H5) reacts with styrene oxide 25 at the higher substituted carbon atom selectively with 59percent retention.
