5432-07-5Relevant academic research and scientific papers
Enantiomerically Pure 5,13-Dicyano-9-oxa[7]helicene: Synthesis and Study
Gupta, Riddhi,Cabreros, Trevor A.,Muller, Gilles,Bedekar, Ashutosh V.
, p. 5397 - 5405 (2018)
Optically pure dicyano oxa[7]helicenes and helicene-like molecules have been prepared and investigated for their optical behavior. The isomers of the intermediate 4,4′-biphenanthrene-3,3′-diol were resolved by physically separating their 1-menthyl carbona
Accelerated Discovery of α-Cyanodiarylethene Photoswitches
Hecht, Stefan,K?nig, Niklas F.,Mutruc, Dragos
supporting information, p. 9162 - 9168 (2021/07/01)
Cyanodiarylethene chromophores are able to undergo constitutional exchange via dynamic covalent chemistry (DCC). During this process, the central ethylene bridge of the molecular scaffold can be broken and thereby enables the assembly of a new combination of aryl moieties around the reformed ethylene bridge. The reversible CC double bond exchange has exemplarily been investigated using α-cyanostilbenes. Establishing a dynamic equilibrium reaction from α-cyanodiarylethene with arylacetonitriles under mild conditions has been the basis to access constitutional libraries of new photoswitches with potentially improved properties. When subject to irradiation with light of adequate wavelength, α-cyanodiarylethenes undergo Z/E isomerization followed by ring-closure. By screening the thus accessible dynamic chromophore libraries using a desired detection wavelength, we could identify specific dithienyl analogues that exhibit three-state photochromism. The combination of dynamic constitutional libraries of functional chromophores in combination with the light-guided screening and selection should lead to more rapid exploration of structural diversity dye chemistry.
Switchable Cobalt-Catalyzed α-Olefination and α-Alkylation of Nitriles with Primary Alcohols
Paudel, Keshav,Xu, Shi,Ding, Keying
supporting information, p. 5028 - 5032 (2021/07/19)
The first switchable α-olefination and α-alkylation of nitriles with primary alcohols catalyzed by a well-defined base transition-metal Co complex was presented. A broad variety of nitriles and primary alcohols are selectively and efficiently converted to the corresponding products by this method. It is noteworthy that the transformation is environmentally benign and atom efficient with H2and H2O being the sole byproducts.
Pyrenedione-Catalyzed α-Olefination of Nitriles under Visible-Light Photoredox Conditions
Bains, Amreen K.,Ankit, Yadav,Adhikari, Debashis
supporting information, p. 2019 - 2023 (2021/04/05)
Herein, we report a combination of pyrenedione (PD) and KOtBu to achieve facile alcohol dehydrogenation under visible-light excitation, where aerobic oxygen is utilized as the terminal oxidant. The resulting carbonyl compound can be easily converted to vinyl nitriles in a single-pot reaction, at 60 °C in 6-8 h. This environmentally benign, organocatalytic approach has distinct advantages over transition-metal-catalyzed α-olefination of nitriles, which often operate at a significantly higher temperature for an extended reaction time.
Manganese Catalyzed α-Alkylation of Nitriles with Primary Alcohols
Jana, Akash,Reddy, C. Bal,Maji, Biplab
, p. 9226 - 9231 (2018/09/21)
The manganese(I) complex bearing a bidentate hydrazone ligand efficiently catalyzes the α-alkylations of nitrile using primary alcohols as alkylating agents. α-Functionalized nitriles were selectively obtained in good to excellent yields. The reaction is environmentally benign, producing water as the sole byproduct. Both benzylic and aliphatic alcohols could be used and functional groups were tolerated.
Synthesis and characterization of phenanthrene derivatives for optoelectronic applications
Raouafi, Sondes,Aloui, Faouzi,Raouafi, Amal,Hassine, Béchir Ben
, p. 697 - 703 (2017/06/13)
New phenanthrene derivatives, bearing cyano group at selected positions, have been prepared in good yields through Knoevenagel condensation and classical oxidative photocyclization. The optical properties of the cyanophenanthrenes have been investigated b
Manganese Catalyzed α-Olefination of Nitriles by Primary Alcohols
Chakraborty, Subrata,Das, Uttam Kumar,Ben-David, Yehoshoa,Milstein, David
supporting information, p. 11710 - 11713 (2017/09/07)
Catalytic α-olefination of nitriles using primary alcohols, via dehydrogenative coupling of alcohols with nitriles, is presented. The reaction is catalyzed by a pincer complex of an earth-abundant metal (manganese), in the absence of any additives, base, or hydrogen acceptor, liberating dihydrogen and water as the only byproducts.
Atmosphere-Controlled Chemoselectivity: Rhodium-Catalyzed Alkylation and Olefination of Alkylnitriles with Alcohols
Li, Junjun,Liu, Yuxuan,Tang, Weijun,Xue, Dong,Li, Chaoqun,Xiao, Jianliang,Wang, Chao
supporting information, p. 14445 - 14449 (2017/10/07)
The chemoselective alkylation and olefination of alkylnitriles with alcohols have been developed by simply controlling the reaction atmosphere. A binuclear rhodium complex catalyzes the alkylation reaction under argon through a hydrogen-borrowing pathway and the olefination reaction under oxygen through aerobic dehydrogenation. Broad substrate scope is demonstrated, permitting the synthesis of some important organic building blocks. Mechanistic studies suggest that the alkylation product may be formed through conjugate reduction of an alkene intermediate by a rhodium hydride, whereas the formation of olefin product may be due to the oxidation of the rhodium hydride complex with molecular oxygen.
Facile Preparation of α-Cyano-α,ω-Diaryloligovinylenes: A New Class of Color-Tunable Solid Emitters
An, Peng,Xu, Nian-Sheng,Zhang, Hao-Li,Cao, Xiao-Ping,Shi, Zi-Fa,Wen, Wei
, p. 1959 - 1966 (2015/09/07)
An efficient Knoevenagel condensation reaction was used to construct a series of α-cyano-α,ω-diaryloligovinylenes, which show prominent fluorescence emission in the solid state. On investigating the effect of conjugation length on fluorescent properties,
Thermal rearrangement of 2,3-diaryl-1-phthalimidoaziridines
Pankova, Alena S.,Sorokina, Mariia V.,Kuznetsov, Mikhail A.
, p. 5381 - 5385 (2015/09/15)
2,3-Diaryl-1-phthalimidoaziridines and 2,3-diaryl-1-phthalimidoaziridine-2-carbonitriles were found to readily undergo thermal rearrangement into imines via 1,2-migration of the phthalimido group and accompanying C-C bond cleavage. Isomerization proceeds regioselectively with preferable migration to the electron-deficient carbon atom. Interestingly, this reaction was found to predominate even in the presence of dipolarophiles.
