132350-97-1Relevant academic research and scientific papers
One-Pot Synthesis of N-H-Free Pyrroles from Aldehydes and Alkynes
Chen, Lai,Huo, Jing-Qian,Kou, Song,Mao, Jianyou,Si, He-Long,Xu, Xin-Yu,Zhang, Jin-Lin
, p. 4348 - 4352 (2021)
The first base-mediated intermolecular cyclization of arylaldehydes and terminal arylacetylenes for the synthesis of a wide range of pyrroles in a single step has been described. The developed methodology used commercially available starting materials and
Asymmetric addition of terminal acetylenes to aldehydes, catalyzed by Zn(OTf)2-cinchona alkaloid complexes
Ekstr?m, Jesper,Zaitsev, Alexey B.,Adolfsson, Hans
, p. 885 - 888 (2006)
Cinchona alkaloids in combination with zinc triflate catalyze the addition of acetylenes to aldehydes at room temperature with ee up to 89% for aliphatic aldehydes. Cinchonidine has proven to be the ligand of choice for the addition reaction whose outcome
Formation of β-Oxo- N-vinylimidates via Intermolecular Ester Incorporation in Huisgen Cyclization/Carbene Cascade Reactions
Wang, Qinxuan,May, Jeremy A.
supporting information, p. 9579 - 9584 (2021/01/09)
Unusual intermolecular trapping of esters by carbenes generated via a Huisgen cyclization/retroelectrocyclization/dediazotization cascade reaction is presented. β-Oxo-N-vinylimidates could be obtained in one step from propargyl carbonazidates. Mechanistic control experiments suggested reversible dipole formation by ester addition to the carbene, and nitrogen attack to the ester carbonyl was irreversibly followed by stereoselective decarboxylative elimination to give the Z-vinyl imidate. The cross-conjugated enone, imidate, and enamine functional groups in the β-oxo-N-vinylimidates offer novel syntheses of functionalized oxazoles.
Regioselective Iron-Catalysed Cross-Coupling Reaction of Aryl Propargylic Bromides and Aryl Grignard Reagents
Manjón-Mata, Inés,Quirós, M. Teresa,Bu?uel, Elena,Cárdenas, Diego J.
supporting information, p. 146 - 151 (2019/12/11)
An iron-catalysed Kumada-type cross-coupling reaction between aryl substituted propargylic bromides and arylmagnesium reagents has been developed. Propargylic coupling products were the main or only outcome, and propargyl/allene regioselectivity was shown to depend on the electronic nature of the substituents on the triple bond of the substrate and on the arylmagnesium halide. Best selectivities were observed when electron donating substituents were present in either reagent. The process is stereoespecific, occurs with configuration inversion and no carbon-based radicals seem to be involved in the mechanism. (Figure presented.).
Alkylation of Terminal Alkynes under Zinc Lewis Acid Catalysis and Its Mechanistic Studies
Osano, Mana,Kida, Takeru,Yonekura, Kyohei,Tsuchimoto, Teruhisa
supporting information, p. 2825 - 2831 (2019/04/13)
With a zinc Lewis acid catalyst and proton sponge in toluene, terminal alkynes were found to undergo the alkylation by alkyl triflates to provide unsymmetrical internal alkynes. This is the first example that a simple alkyl chain other than benzylic and norbornyl units can be introduced onto the alkynyl carbon atom under Lewis acid catalysis. Mechanistic studies revealed that the activation of the alkyne by the zinc Lewis acid and proton sponge is the trigger of the reaction to give a monoalkynylzinc species, which successively reacts with the alkyl triflate to afford the internal alkyne. A radical pathway is unlikely in this system. (Figure presented.).
Transition-metal-free C-C σ-bond activation of α-aryl ketones and subsequent Zn-catalyzed intramolecular cyclization: synthesis of tetrasubstituted furans
Yuan, Yang,Tan, Hailu,Kong, Lingkai,Zheng, Zhong,Xu, Murong,Huang, Jiaqi,Li, Yanzhong
, p. 2725 - 2733 (2019/03/12)
A highly atom-economical protocol for the synthesis of tetrasubstituted furans has been developed. This process is realized through the tandem reactions of Cs2CO3 promoted C-C σ-bond activation of α-aryl ketones followed by Zn-cataly
Iron-Catalyzed Coupling of Propargyl Bromides and Alkyl Grignard Reagents
Domingo-Legarda, Pablo,Soler-Yanes, Rita,Quirós-López, M. Teresa,Bu?uel, Elena,Cárdenas, Diego J.
supporting information, p. 4900 - 4904 (2018/09/10)
An iron-catalyzed Kumada-type cross-coupling reaction of propargyl halides with alkylmagnesium reagents is described. The reaction is fast, takes place in smooth conditions, tolerates several functional groups that would be able to react with the Grignard reagent, and may afford either allene or propargyl coupling derivatives. Factors involved in the observed regioselectivity have been studied.
Lewis-base-catalysed selective reductions of ynones with a mild hydride donor
Sch?mberg,Zi,Vilotijevic
, p. 3266 - 3269 (2018/04/05)
Ynones are efficiently reduced with a mild hydride donor in the presence of a catalytic amount of nucleophilic phosphines. The reactions are selective 1,2-reductions that give propargyl alcohols in yields of up to 96%. It is proposed that success in these reactions depends on the activation of ynones by a Lewis base catalyst. A protic additive plays a key role in suppressing the undesired reaction pathways and accelerating the 1,2-reductions.
NiICatalyzes the Regioselective Cross-Coupling of Alkylzinc Halides and Propargyl Bromides to Allenes
Soler-Yanes, Rita,Arribas-álvarez, Iván,Guisán-Ceinos, Manuel,Bu?uel, Elena,Cárdenas, Diego J.
supporting information, p. 1584 - 1590 (2017/02/10)
We describe the unprecedented formation of allenes by Ni-catalyzed cross-coupling of propargyl bromides with alkylzinc halides. The reaction regioselectivity is complementary to the previously reported formation of propargyl-coupled compounds. Experiments
On the Distribution of Linear versus Angular Naphthalenes in Aromatic Tetradehydro-Diels–Alder Reactions – Effect of Linker Structure and Steric Bulk
Chinta, Bhavani Shankar,Baire, Beeraiah
supporting information, p. 3381 - 3385 (2017/06/29)
We report here a systematic study of the aromatic tetradehydro-Diels–Alder (Ar-TDDA) reaction to elucidate the factors that have significant effects on the distribution of linear and angular naphthalene products. Two factors were studied, that is, the nat
