Lewis acid-catalyzed tandem cyclization of in situ generated o-quinone methides and arylsulfonyl hydrazides for a one-pot entry to 3-sulfonylbenzofurans

2019 ◽  
Vol 6 (24) ◽  
pp. 3929-3933 ◽  
Author(s):  
Fan-Xiao Meng ◽  
Ruo-Nan Wang ◽  
Hong-Li Huang ◽  
Shu-Wen Gong ◽  
Qian-Li Li ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Quinone Methides ◽  
One Pot ◽  
Acid Catalyzed ◽  
Tandem Cyclization ◽  
First Time

Lewis acid-mediated one-pot tandem cyclization of o-QMs with arylsulfonyl hydrazides was described for the first time and the corresponding 3-sulfonylbenzofuran products were obtained in moderate to good yields.

Organocatalytic site- and stereoselective 1,6-additions of N-aryl-3-oxobutanamides to propargylic aza-p-quinone methides

2020 ◽  
Vol 7 (21) ◽  
pp. 3446-3451
Author(s):  
Fushuai Li ◽  
Xuling Chen ◽  
Shuai Liang ◽  
Zhenyan Shi ◽  
Pengfei Li ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Conjugate Addition ◽  
Quinone Methides ◽  
Propargylic Alcohols ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed ◽  
Site Selective ◽  
First Time

A chiral phosphoric acid catalyzed site-selective 1,6-conjugate addition of N-aryl-3-oxobutanamides to in situ formed propargylic aza-p-quinone methides from propargylic alcohols has been established for the first time.

Lewis Acid Catalyzed Tandem 1,4-Conjugate Addition/Cyclization of in Situ Generated Alkynyl o-Quinone Methides and Electron-Rich Phenols: Synthesis of Dioxabicyclo[3.3.1]nonane Skeletons

2018 ◽  
Vol 20 (14) ◽  
pp. 4371-4374 ◽  
Author(s):  
Ji-Yuan Du ◽  
Yan-Hua Ma ◽  
Fan-Xiao Meng ◽  
Bao-Li Chen ◽  
Shao-Liang Zhang ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Conjugate Addition ◽  
Quinone Methides ◽  
Acid Catalyzed

Catalytic Carbonyl-Olefin Metathesis of Aliphatic Ketones: Iron(III) HomoDimers as Lewis Acidic Superelectrophiles

2018 ◽  
Author(s):  
Haley Albright ◽  
Paul S. Riehl ◽  
Christopher C. McAtee ◽  
Jolene P. Reid ◽  
Jacob R. Ludwig ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Olefin Metathesis ◽  
Acid Activation ◽  
Lewis Acid Catalysts ◽  
Distinct Mode ◽  
Aliphatic Ketones ◽  
Carbon Carbon Bond ◽  
Metathesis Reactions ◽  
Acid Catalyzed

<div>Catalytic carbonyl-olefin metathesis reactions have recently been developed as a powerful tool for carbon-carbon bond</div><div>formation. However, currently available synthetic protocols rely exclusively on aryl ketone substrates while the corresponding aliphatic analogs remain elusive. We herein report the development of Lewis acid-catalyzed carbonyl-olefin ring-closing metathesis reactions for aliphatic ketones. Mechanistic investigations are consistent with a distinct mode of activation relying on the in situ formation of a homobimetallic singly-bridged iron(III)-dimer as the active catalytic species. These “superelectrophiles” function as more powerful Lewis acid catalysts that form upon association of individual iron(III)-monomers. While this mode of Lewis acid activation has previously been postulated to exist, it has not yet been applied in a catalytic setting. The insights presented are expected to enable further advancement in Lewis acid catalysis by building upon the activation principle of “superelectrophiles” and broaden the current scope of catalytic carbonyl-olefin metathesis reactions.</div>

A heavy metal- and oxidant-free, one-pot synthesis of pyridines and fused pyridines based on a Lewis acid-catalyzed multicomponent reaction

2014 ◽  
Vol 50 (82) ◽  
pp. 12270-12272 ◽  
Author(s):  
V. P. Alex Raja ◽  
Giammarco Tenti ◽  
Subbu Perumal ◽  
J. Carlos Menéndez
Keyword(s):  
Heavy Metal ◽  
Lewis Acid ◽  
Multicomponent Reaction ◽  
One Pot ◽  
One Pot Synthesis ◽  
Acid Catalyzed

Pyridines and fused pyridines are accessible by a combination of a Lewis acid-catalyzed multicomponent reaction and aromatization involving loss of a 2-furylmethyl chain.

Synthesis of 4-styrylcoumarins via FeCl3-promoted cascade reactions of propargylamines with β-keto esters

2019 ◽  
Vol 17 (16) ◽  
pp. 4005-4013 ◽  
Author(s):  
Li-Qin Yan ◽  
Xiaoting Cai ◽  
Xinwei He ◽  
Hui Wang ◽  
Mengqing Xie ◽  
...  
Keyword(s):  
Cascade Reactions ◽  
Cyclization Reaction ◽  
Quinone Methides ◽  
Keto Esters ◽  
Tandem Cyclization

A versatile and highly regioselective FeCl3-promoted tandem cyclization reaction of in situ generated alkynyl o-quinone methides (o-AQMs) with β-keto esters has been developed.

scholarly journals A three-component, Zn(OTf)2-mediated entry into trisubstituted 2-aminoimidazoles

2019 ◽  
Vol 15 ◽  
pp. 1061-1064 ◽  
Author(s):  
Alexei Lukin ◽  
Anna Bakholdina ◽  
Anna Kryukova ◽  
Alexander Sapegin ◽  
Mikhail Krasavin
Keyword(s):  
Lewis Acid ◽  
Primary Amine ◽  
Three Component Reaction ◽  
Acid Catalyzed ◽  
In Situ Generation

A three-component reaction involving in situ generation of propargylureas and subsequent Zn(OTf)2-mediated cyclocondensation with a primary amine yielded trisubstituted 2-aminoimidazoles. These findings are in contrast to the previously reported base-promoted unimolecular cyclization of propargylureas (leading to 2-imidazolones) and extend the range of Lewis acid-catalyzed azole syntheses based on N-carbonyl propargylamines.

ChemInform Abstract: Lewis Acid Catalyzed Procedure for Selective Conversion of the Carbocyclic Diels-Alder Adducts of Danishefsky′s Diene to 2-Cyclohexenones and Its Extension to Their One-Pot Syntheses.

ChemInform ◽  
2001 ◽  
Vol 32 (8) ◽  
pp. no-no
Author(s):  
Tsutomu Inokuchi ◽  
Masamitsu Okano ◽  
Tomoko Miyamoto ◽  
Hariyani Bte Madon ◽  
Masaki Takagi
Keyword(s):  
Lewis Acid ◽  
Diels Alder ◽  
One Pot ◽  
Selective Conversion ◽  
Acid Catalyzed

Metal-Free One-Pot Synthesis of 3-Phosphinoylbenzofurans via Phospha-Michael Addition/Cyclization of H-Phosphine Oxides and in Situ Generated ortho-Quinone Methides

2018 ◽  
Vol 20 (2) ◽  
pp. 477-480 ◽  
Author(s):  
Ji-Yuan Du ◽  
Yan-Hua Ma ◽  
Rui-Qing Yuan ◽  
Nana Xin ◽  
Shao-Zhen Nie ◽  
...  
Keyword(s):  
Michael Addition ◽  
Phosphine Oxides ◽  
Quinone Methides ◽  
One Pot ◽  
Metal Free ◽  
One Pot Synthesis
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