40290-63-9Relevant academic research and scientific papers
Dynamic Kinetic Cross-Electrophile Arylation of Benzyl Alcohols by Nickel Catalysis
Guo, Peng,Wang, Ke,Jin, Wen-Jie,Xie, Hao,Qi, Liangliang,Liu, Xue-Yuan,Shu, Xing-Zhong
supporting information, p. 513 - 523 (2021/01/12)
Catalytic transformation of alcohols via metal-catalyzed cross-coupling reactions is very important, but it typically relies on a multistep procedure. We here report a dynamic kinetic cross-coupling approach for the direct functionalization of alcohols. The feasibility of this strategy is demonstrated by a nickel-catalyzed cross-electrophile arylation reaction of benzyl alcohols with (hetero)aryl electrophiles. The reaction proceeds with a broad substrate scope of both coupling partners. The electron-rich, electron-poor, and ortho-/meta-/para-substituted (hetero)aryl electrophiles (e.g., Ar-OTf, Ar-I, Ar-Br, and inert Ar-Cl) all coupled well. Most of the functionalities, including aldehyde, ketone, amide, ester, nitrile, sulfone, furan, thiophene, benzothiophene, pyridine, quinolone, Ar-SiMe3, Ar-Bpin, and Ar-SnBu3, were tolerated. The dynamic nature of this method enables the direct arylation of benzylic alcohol in the presence of various nucleophilic groups, including nonactivated primary/secondary/tertiary alcohols, phenols, and free indoles. It thus offers a robust alternative to existing methods for the precise construction of diarylmethanes. The synthetic utility of the method was demonstrated by a concise synthesis of biologically active molecules and by its application to peptide modification and conjugation. Preliminary mechanistic studies revealed that the reaction of in situ formed benzyl oxalates with nickel, possibly via a radical process, is an initial step in the reaction with aryl electrophiles.
Visible-Light-Driven, Copper-Catalyzed Decarboxylative C(sp3)?H Alkylation of Glycine and Peptides
Wang, Chao,Guo, Mengzhun,Qi, Rupeng,Shang, Qinyu,Liu, Qiang,Wang, Shan,Zhao, Long,Wang, Rui,Xu, Zhaoqing
supporting information, p. 15841 - 15846 (2018/11/23)
Despite a well-developed and growing body of work in Cu catalysis, the potential of Cu to serve as a photocatalyst remains underexplored. Reported herein is the first example of visible-light-induced Cu-catalyzed decarboxylative C(sp3)?H alkylation of glycine for preparing α-alkylated unnatural α-amino acids. It merits mentioning that the mild conditions and the good functional-group tolerance allow the modification of peptides using this method. The mechanistic studies revealed that a radical–radical coupling pathway is involved in the reaction.
Amide and Peptide Bond Formation in Water at Room Temperature
Gabriel, Christopher M.,Keener, Megan,Gallou, Fabrice,Lipshutz, Bruce H.
supporting information, p. 3968 - 3971 (2015/09/01)
A general and environmentally responsible method for the formation of amide/peptide bonds in an aqueous micellar medium is described. Use of uronium salt (1-cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylaminomorpholinocarbenium hexafluorophosphate (COMU) as a coupling reagent, 2,6-lutidine, and TPGS-750-M represents mild conditions associated with these valuable types of couplings. The aqueous reaction medium is recyclable leading to low E Factors.
A one-pot saponification-coupling sequence suitable for C-terminus peptide elongation using lithium carboxylates
Azzouz, Rabah,Petit, Sylvain,Rouchet, Jean-Baptiste,Bischoff, Laurent
supporting information, p. 1843 - 1846 (2014/08/18)
An efficient procedure has been developed for the saponification of common peptide esters, followed by straightforward coupling of the lithium carboxylate. Adding some water to the reaction medium gave faster saponification and did not interfere with the coupling reagent. As peptide chemistry constitutes a major application of the amidation reaction, amino acid substrates were chosen for this study, monitoring both yields and epimerization of the peptides obtained. Georg Thieme Verlag Stuttgart New York.
Synthesis and electrochemical studies of disubstituted ferrocene/dipeptide conjugates with sulfur-containing side chains
Scully, Conor C.G.,Rutledge, Peter J.
scheme or table, p. 5653 - 5659 (2010/10/02)
A series of 1 1'-disubstituted ferrocenoyl peptides incorporating dipeptide sidearms has been synthesized and studied electrochemically. The target peptides include ferrocene as an electrochemical reporter, sulfur-containing amino acids (L-methionine, S-methyl-L-cysteine, S-trityl-L-cysteine, S-benzhydryl-L- cysteine) as metal binding agents, and amino acids with non-polar side chains (L-alanine, L-valine, L-phenylalanine) as spacers between reporter and metal binding groups. Ferrocene/dipeptide conjugates were prepared using solution phase peptide synthesis methods employing a BOC-protecting group strategy and HBTU- (O-(benzotriazol-1-yl)-N, N, N', N'-tetramethyluronium hexafluorophosphate) mediated peptide coupling. The electrochemical properties of these 1, 1'-substituted ferrocenoyl peptides have been characterized using cyclic voltammetry. All exhibit fully reversible one electron oxidation steps; forward sweep half wave peaks (EF), reverse sweep half wave peaks (ER), peak separations (DEP) and half wave potentials (E1/2) are reported. Finally, towards the goal of utilizing ferrocenoyl peptides to detect heavy metals in solution, the response of these ferrocene/dipeptide conjugates to metal cations (zinc(II), mercury(II), cadmium(II), lead(II), silver(I)) has been examined. Monitoring changes in the potential of the Fe(II)/Fe(III) redox couple to follow peptide/metal interactions, we have probed the influence of the spacer unit between the redox reporter and the metal-binding amino acid, and shown that these systems respond to mercury(II) more strongly than to other heavy metal ions.
Synthesis and biological evaluation of potential bisubstrate inhibitors of protein farnesyltransferase. Design and synthesis of functionalized imidazoles
De Figueiredo, Renata Marcia,Coudray, Laetitia,Dubois, Joelle
, p. 3299 - 3309 (2008/09/20)
A novel series of compounds, derived from 2,5-functionalized imidazoles, have been synthesized as potential bisubstrate inhibitors of protein farnesyltransferase (FTase) using structure-based design. These compounds have a 1,4-diacid chain and a tripeptid
Convenient high yielding gram scale solution synthesis of methionine-enkephalin
Masiukif.wicx, Elzbieta,Rzeszotarska, Barbara
, p. 1672 - 1675 (2007/10/03)
A simple, large-scale synthesis of a cytokine, methionine-enkephalin, Tyr-Gly-Gly-Phe-Met, has been elaborated. Classical solution peptide chemistry methods without protection of amino acid side-chain functions and l+(2+2) segment condensation were used. A nine-step synthesis from commercial amino acid derivatives was developed with yields ranging from 86% to 99%, averaging 92%. The purity of all intermediates was found to be 99.0-100% by HPLC. The process has been used to prepare greater than 150 g quantities of the pentapeptide as a monohydrate of 100% purity. Hydantoin formation was observed during saponification of Boc-TyrGly-Gly-Phe-Met-OMe and minimised.
A new coupling reagent for peptide synthesis. Benzotriazolvyloxy-bis (pyrroltdino) -carbonium hexaflouorophosphate (BBC)
Chen, Shaoqing,Xu, Jiecheng
, p. 647 - 650 (2007/10/02)
Benzotriazolyloxy-bis(pyrrolidino)-carbonium hexa- fluorophosphate (BBC) is found to be a new excellent coupling reagent devoid of cytotoxic by-product instead of HBTU and BOP. It has been applied in the solution and solid phase peptide synthesis.
PENTAFLUOROPHENYL DIPHENYLPHOSPHINATE A NEW EFFICIENT COUPLING REAGENT IN PEPTIDE CHEMISTRY
Chen, Shaoqing,Xu, Jiecheng
, p. 6711 - 6714 (2007/10/02)
Pentafluorophenyl diphenylphosphinate was found to be a new efficient coupling reagent for the racemization-free synthesis of peptides.It has been applied in both the solution and the solid phase peptide synthesis.
THE CINNAMYLOXYCARBONYL GROUP AS A NEW AMINO-PROTECTING GROUP
Kinoshita, Hideki,Inomata, Katsuhiko,Kameda, Takuo,Kotake, Hiroshi
, p. 515 - 518 (2007/10/02)
A new urethane-type protecting group for amines, cinnamyloxycarbonyl (Coc) group, is described.The cleavage of the Coc group is effectively catalyzed by 5 molpercent of in the presence of formic acid, pyridine, and N-hydroxysuccinimide in ref
