1329059-04-2Relevant academic research and scientific papers
Mild-Base-Promoted Arylation of (Hetero)Arenes with Anilines
Monzón, Diego M.,Santos, Tanausú,Pinacho-Crisóstomo,Martín, Víctor S.,Carrillo, Romen
, p. 325 - 333 (2018)
Transition metal-free radical arylation of heteroarenes is achieved at room temperature by simply adding aqueous sodium carbonate to a solution of the corresponding heteroarene and arenediazonium salt, which can even be formed in situ. Such an easy, inexpensive and mild methodology has been optimized and applied to the expeditious modification of interesting molecular cores like naphthylimide or bisthienylcyclopentenes.
Alternating current electrolysis for organic electrosynthesis: Trifluoromethylation of (hetero)arenes
Rodrigo, Sachini,Um, Chanchamnan,Mixdorf, Jason C.,Gunasekera, Disni,Nguyen, Hien M.,Luo, Long
, p. 6719 - 6723 (2020)
Paired electrolysis has a limited reaction scope for organic synthesis because it is often not compatible with reactions involving short-lived intermediates. We addressed this limitation using alternating current electrolysis (ACE). Using trifluoromethyla
A general copper-based photoredox catalyst for organic synthesis: Scope, application in natural product synthesis and mechanistic insights
Deldaele, Christopher,Michelet, Bastien,Baguia, Hajar,Kajouj, Sofia,Romero, Eugenie,Moucheron, Cecile,Evano, Gwilherm
, p. 621 - 629 (2018/10/04)
Organic transformations can broadly be classified into four categories including cationic, anionic, pericyclic and radical reactions. While the last category has been known for decades to provide remarkably efficient synthetic pathways, it has long been hampered by the need for toxic reagents, which considerably limited its impact on chemical synthesis. This situation has come to an end with the introduction of new concepts for the generation of radical species, photoredox catalysis – which simply relies on the use of a catalyst that can be activated upon visible light irradiation – certainly being the most efficient one. The state-of-the-art catalysts mostly rely on the use of ruthenium and iridium complexes and organic dyes, which still considerably limits their broad implementation in chemical processes: alternative readily available catalysts based on inexpensive, environmentally benign base metals are therefore strongly needed. Furthermore, expanding the toolbox of methods based on photoredox catalysis will facilitate the discovery of new light-mediated transformations. This article details the use of a simple copper complex which, upon activation with blue light, can initiate a broad range of radical reactions.
Molecular Design of Donor-Acceptor-Type Organic Photocatalysts for Metal-free Aromatic C?C Bond Formations under Visible Light
Wang, Lei,Byun, Jeehye,Li, Run,Huang, Wei,Zhang, Kai A. I.
, p. 4312 - 4318 (2018/10/02)
Metal-free and photocatalytic radical-mediated aromatic C?C bond formations offer a promising alternative pathway to the conventional transition metal-catalyzed cross-coupling reactions. However, the formation of aryl radicals from common precursors such as aryl halides is highly challenging due to their extremely high reductive potential. Here, we report a structural design strategy of donor-acceptor-type organic photocatalysts for visible light-driven C?C bond formations through the reductive dehalogenation of aryl halides. The reduction potential of the photocatalysts could be systematically aligned to be ?2.04 V vs. SCE via a simple heteroatom engineering of the donor-acceptor moieties. The high reductive potential of the molecular photocatalyst could reduce various aryl halides into aryl radicals to form the C?C bond with heteroarenes. The designability of the molecular photocatalyst further allowed the synthesis of a high LUMO (lowest unoccupied molecular orbital) polymer photocatalyst by a self-initiated free radical polymerization without compromising its LUMO level. (Figure presented.).
A General Copper Catalyst for Photoredox Transformations of Organic Halides
Michelet, Bastien,Deldaele, Christopher,Kajouj, Sofia,Moucheron, Cécile,Evano, Gwilherm
supporting information, p. 3576 - 3579 (2017/07/17)
A broadly applicable copper catalyst for photoredox transformations of organic halides is reported. Upon visible light irradiation in the presence of catalytic amounts of [(DPEphos)(bcp)Cu]PF6 and an amine, a range of unactivated aryl and alkyl halides were shown to be smoothly activated through a rare Cu(I)/Cu(I)?/Cu(0) catalytic cycle. This complex efficiently catalyzes a series of radical processes, including reductions, cyclizations, and direct arylation of arenes.
A family of low molecular-weight, organic catalysts for reductive C-C bond formation
Shaaban, Saad,Jolit, Ana?s,Petkova, Desislava,Maulide, Nuno
, p. 13902 - 13905 (2015/09/15)
Hydrazines form a new family of low molecular-weight reducing agents for diazonium salts. Using only small amounts of hydrazine catalyst, the coupling of diazonium salts to a variety of reactive partners has been achieved, without the requirement for either metal adjuvants or irradiation with visible or ultraviolet light. The generality of the concept proposed herein as well as its advantages in the preparative scale is outlined and discussed.
Copper-catalyzed free-radical C-H arylation of pyrroles
Honraedt, Aurélien,Raux, Marie-Audrey,Grognec, Erwan Le,Jacquemin, Denis,Felpin, Fran?ois-Xavier
supporting information, p. 5236 - 5238 (2014/05/06)
A room temperature copper-catalyzed radical arylation of pyrroles with anilines, through in situ generated aryl diazonium salts, has been developed under neutral conditions. Experimental and theoretical studies explain the crucial role of CaCO3 and the high regioselectivity observed. the Partner Organisations 2014.
Identification of a novel conformationally constrained glucagon receptor antagonist
Lee, Esther C.Y.,Tu, Meihua,Stevens, Benjamin D.,Bian, Jianwei,Aspnes, Gary,Perreault, Christian,Sammons, Matthew F.,Wright, Stephen W.,Litchfield, John,Kalgutkar, Amit S.,Sharma, Raman,Didiuk, Mary T.,Ebner, David C.,Filipski, Kevin J.,Brown, Janice,Atkinson, Karen,Pfefferkorn, Jeffrey A.,Guzman-Perez, Angel
, p. 839 - 844 (2014/02/14)
Identification of orally active, small molecule antagonists of the glucagon receptor represents a novel treatment paradigm for the management of type 2 diabetes mellitus. The present work discloses novel glucagon receptor antagonists, identified via confo
Self-sorting self-complementary assemblies of π-conjugated acyclic anion receptors
Maeda, Hiromitsu,Kinoshita, Kota,Naritani, Kazumasa,Bando, Yuya
supporting information; experimental part, p. 8241 - 8243 (2011/09/16)
Pyrrole-based π-conjugated anion-responsive molecules bearing an anionic moiety form self-complementary dimers, which exhibit self-sorting behaviours depending on the substituted positions of anionic sites.
