35448-14-7Relevant academic research and scientific papers
Metal-, Photocatalyst-, and Light-Free Minisci C-H Alkylation of N-Heteroarenes with Oxalates
Dong, Jianyang,Wang, Zhen,Wang, Xiaochen,Song, Hongjian,Liu, Yuxiu,Wang, Qingmin
, p. 7532 - 7540 (2019/06/14)
Herein, we report a mild protocol for metal-, photocatalyst-, and light-free Minisci C-H alkylation reactions of N-heteroarenes with alkyl oxalates derived from primary, secondary, and tertiary alcohols. The protocol uses environmentally benign persulfate
Total Synthesis of Emmyguyacins A and B, Potential Fusion Inhibitors of Influenza Virus
Jana, Santanu,Sarpe, Vikram A.,Kulkarni, Suvarn S.
supporting information, p. 6938 - 6942 (2018/10/25)
Fungal glycolipids emmyguyacins A and B inhibit the pH-dependent conformational change of hemaglutinin A during replication of the Influenza virus. Herein, we report the first total synthesis and structure confirmation of emmyguyacins A and B. Our efficient route, which involves regioselective functionalization of trehalose, allows rapid access to adequate amounts of chemically pure emmyguyacin analogues including the desoxylate derivatives for SAR studies.
Alcohols as Latent Coupling Fragments for Metallaphotoredox Catalysis: Sp3-sp2 Cross-Coupling of Oxalates with Aryl Halides
Zhang, Xiaheng,MacMillan, David W.C.
supporting information, p. 13862 - 13865 (2016/11/06)
Alkyl oxalates, prepared from their corresponding alcohols, are engaged for the first time as carbon radical fragments in metallaphotoredox catalysis. In this report, we demonstrate that alcohols, native organic functional groups, can be readily activated with simple oxalyl chloride to become radical precursors in a net redox-neutral Csp3-Csp2 cross-coupling with a broad range of aryl halides. This alcohol-activation coupling is successfully applied to the functionalization of a naturally occurring steroid and the expedient synthesis of a medicinally relevant drug lead.
Nitroxyl radical/PhI(OAc)2: One-pot oxidative cleavage of vicinal diols to (di)carboxylic acids
Shibuya, Masatoshi,Shibuta, Takuro,Fukuda, Hayato,Iwabuchi, Yoshiharu
supporting information, p. 5010 - 5013 (2013/01/15)
A mild and user-friendly one-pot oxidative cleavage of vicinal diols to their corresponding (di)carboxylic acids using AZADOs and PhI(OAc)2 is described. 1,2-Diols and 2,3-diols as well as 1,2,3-triol gave one- or two-carbon-unit-shorter carboxylic acids. Internal vicinal diols also smoothly underwent one-pot oxidative cleavage to afford the corresponding dicarboxylic acids. Cyclic vicinal diols are converted to their corresponding open-form dicarboxylic acids.
Catalytic phosphorus(V)-mediated nucleophilic substitution reactions: Development of a catalytic appel reaction
Denton, Ross M.,An, Jie,Adeniran, Beatrice,Blake, Alexander J.,Lewis, William,Poulton, Andrew M.
, p. 6749 - 6767 (2011/10/02)
Catalytic phosphorus(V)-mediated chlorination and bromination reactions of alcohols have been developed. The new reactions constitute a catalytic version of the classical Appel halogenation reaction. In these new reactions oxalyl chloride is used as a consumable stoichiometric reagent to generate the halophosphonium salts responsible for halogenation from catalytic phosphine oxides. Thus, phosphine oxides have been transformed from stoichiometric waste products into catalysts and a new concept for catalytic phosphorus-based activation and nucleophilic substitution of alcohols has been validated. The present study has focused on a full exploration of the scope and limitations of phosphine oxide catalyzed chlorination reactions as well as the development of the analogous bromination reactions. Further mechanistic studies, including density functional theory calculations on proposed intermediates of the catalytic cycle, are consistent with a catalytic cycle involving halo- and alkoxyphosphonium salts as intermediates.
SELECTIVE MONOETHERIFICATION AND MONOESTERIFICATION OF DIOLS AND DIACIDS UNDER PHASE-TRANSFER CONDITIONS
Zerda, Jaime de la,Barak, Gabriela,Sasson, Yoel
, p. 1533 - 1536 (2007/10/02)
Research on the selectivity of etherification reactions of diols and esterification reactions of diacids by alkyl halides under phase-transfer catalysis has shown that under such conditions, selectivity of monoetherification increases in the order prim sec tert diols, though overall yield of monoether decreases from sec to tert diols.Monoesterification of diacids was accomplished with a high degree of selectivity.Optimal extraction of diols and diacids was found to correspond in general to chain lengths of around 5 carbons.This could mean that the complex formed between the catalyst and the anion to react is stabilized for certain carbon lengths by inner solvation in virtue of its spatial conformation.
