- DIPROTONATION OF NITROARENES
-
Cryoscopic measurements shows that 1-nitronaphthalene is diprotonated in trifluoromethanesulfonic acid (TFSA).The diprotonated nitronaphthalenes are N,N-dihydroxyiminiumnaphthalenium dications, wich are fully characterised by UV, 1H-, 13/
- Ohta, Toshiharu,Shudo, Koichi,Okamoto, Toshihiko
-
-
Read Online
- Atroposelective Synthesis, Structure and Properties of a Novel Class of Axially Chiral N-Aryl Quinolinium Salt
-
Inspired by naturally occurring molecules containing atropisomeric N+-C axes, we have developed a novel synthetic approach to generate a library of axially chiral N-aryl quinolinium salts. Enantiopurities up to 93 % ee were obtained via a four-step route from commercially available precursors. Axial stereochemistry was controlled through an enantioselective ring-closing Buchwald–Hartwig coupling reaction. The structure and properties of the salts were examined by X-ray crystallography, DFT, UV-Vis, and fluorescence spectroscopy, revealing high rotational barriers and solvatochromic behaviour.
- Sweet, Jamie S.,Rajkumar, Sundaram,Dingwall, Paul,Knipe, Peter C.
-
p. 3980 - 3985
(2021/03/31)
-
- Additive-free radical cascade reaction of oxime esters: Synthesis of pyrroline-functionalized phenanthridines
-
A variety of dihydropyrrole-functionalized phenanthridines were efficiently synthesized by the metal-free, radical cascade cyclization reaction of 2-isocyanobiphenyls with γ,δ- unsaturated oxime esters. The C-N/C-C/C-C bonds were formed via the oil bath method in a one-pot procedure with broad substrate applicability. The radical process was supported by kinetic isotope effect studies and radical inhibition studies.
- Shao, Liming,Xue, Yijie,Xue, Dengqi,He, Qian,Ge, Qianwei,Li, Wei
-
p. 12284 - 12293
(2020/11/10)
-
- Direct intermolecular aniline ortho- arylation via benzyne intermediates
-
A method for direct, transition-metal-free ortho-arylation of anilines by aryl chlorides, bromides, fluorides, and triflates has been developed. This methodology provides the most direct approach to 2-arylanilines since no protecting or directing groups on nitrogen are required. The arylation is functional-group tolerant, with alkene, ether, trifluoromethyl, dimethylamino, carbonyl, chloro, and cyano functionalities tolerated. Phenylation of enantiopure binaphthyldiamine affords a product with >99% ee.
- Truong, Thanh,Daugulis, Olafs
-
supporting information
p. 5964 - 5967
(2013/02/22)
-
- Palladium-catalyzed asymmetric dearomatization of naphthalene derivatives
-
(Chemical Equation Presented) An intramolecular enantioselective metal-catalyzed dearomatization reaction is described. This procedure allows the dearomatization of naphthalene derivatives through an electrophilic aromatic substitution-type reaction on a
- Garcia-Fortanet, Jorge,Kessler, Florian,Buchwald, Stephen L.
-
supporting information; experimental part
p. 6676 - 6677
(2009/10/30)
-
- Mechanistic study on rearrangement cascades starting from annulated 2-Aza-hepta-2,4-dienyl-6-ynyl anions: Formation of aniline and azepine derivatives
-
Deprotonation of benzothiophene-derived alkynyl imine 11 with lithium diisopropylamide (LDA) and subsequent transmetalation with ZnCl2 etherate furnished azepine 12 upon aqueous workup. Similarly, alkynyl benzaldimine la gave a mixture of benza
- Lyaskovskyy, Volodymyr,Froehlich, Roland,Wuerthwein, Ernst-Ulrich
-
p. 3113 - 3119
(2008/02/05)
-
- Radical nucleophilic substitution of 2-(4-halophenyl)-2-methyl-1- chloropropane with enolate ions of ketones
-
(Chemical Equation Presented) The photoinitiated reaction of 2-(4-halophenyl)-2-methyl-1-chloropropane 2a,b (halogen = Br, I, respectively) with the anions of pinacolone (3a) and acetophenone (3b) either in DMSO or in liquid ammonia are reported. In DMSO,
- Pierini, Adriana B.,Gallego, Mariana H.,Andrada, Karina F. Crespo
-
p. 3089 - 3092
(2008/02/05)
-