Electrochemical Synthesis for Phosphorylated Amino Acid Derivatives DOI

Synfacts, Journal Year: 2023, Volume and Issue: 19(06), P. 0632 - 0632

Published: May 11, 2023

Key words electrochemical synthesis - C(sp3)–H functionalization phosphorylated amino acids

Language: Английский

Visible-light induced direct C(sp3)–H functionalization: recent advances and future prospects DOI
Jia‐Lin Tu, Yining Zhu, Pengcheng Li

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(18), P. 5278 - 5305

Published: Jan. 1, 2024

This review summarizes the latest methodological advances in photocatalytic C(sp 3 )–H functionalization, with a particular emphasis on formation of C–P, C–B, C–S bonds, etc ., and some prominent efforts asymmetric C–H functionalization.

Language: Английский

Citations

17
Recent Progress in Electrochemical Modification of Amino Acids and Peptides DOI

Xinyue Fang,

Yawen Huang,

Xinwei Hu

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(3), P. 903 - 903

Published: Jan. 1, 2024

Language: Английский

Citations

8
Photocatalytic redox-neutral α-C(sp3)–H pyridination of glycine derivatives and N-arylamines with cyanopyridines DOI
Changduo Pan, Dongdong Chen, Yangjian Cheng

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(33), P. 4451 - 4454

Published: Jan. 1, 2024

Photocatalytic α-C(sp 3 )–H pyridination of N -arylglycine derivatives and -arylamines with cyanopyridines was developed through radical–radical cross-coupling under redox-neutral conditions.

Language: Английский

Citations

7
Recent advances in the electrochemical synthesis of organophosphorus compounds DOI Creative Commons
Babak Kaboudin, Milad Behroozi,

Sepideh Sadighi

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 21, P. 770 - 797

Published: April 16, 2025

In this review, we describe recent advances in electrochemical green methods for the synthesis of various organophosphorus compounds through formation phosphorus–carbon, phosphorus–nitrogen, phosphorus–oxygen, phosphorus–sulfur, and phosphorus–selenium bonds. The impact different electrodes is also discussed matter. Graphite, platinum, RVC, nickel have been used extensively compounds. made method a promising preparing structures. This review an introduction to encourage scientists use electrosynthesis as green, precise, low-cost prepare phosphorous

Language: Английский

Citations

1
Stabilized Carbon‐Centered Radical‐Mediated Carbosulfenylation of Styrenes: Modular Synthesis of Sulfur‐Containing Glycine and Peptide Derivatives DOI Creative Commons
Zihui Yang, Jia Liu, Lan‐Gui Xie

et al.

Advanced Science, Journal Year: 2024, Volume and Issue: 11(29)

Published: June 9, 2024

Abstract Sulfur‐containing amino acids and peptides play critical roles in organisms. Thiol‐ene reactions between the thiol residues of L ‐cysteine alkenyl fragments designed coupling partners serve as primary tools for constructing C─S bonds synthesis unnatural sulfur‐containing acid derivatives. These are favored due to preference hydrogen transfer from β‐sulfanyl carbon radical intermediates. In this paper, study proposes utilizing carbon‐centered radicals stabilized by capto‐dative effect, generated under photocatalytic conditions N –aryl glycine The aim is compete with hydrogen, enabling C─C bond formation radicals. This protocol robust presence air water, offers significant potential a modular efficient platform synthesizing modifying peptides, particularly abundant disulfides styrenes.

Language: Английский

Citations

6
TEMPO/PhI(OAc)2 promotes the α-aminophosphinoylation of alcohols with amines and H-phosphine oxides in aqueous medium DOI

Qiang Huang,

Xin Jin,

Lvjia Wu

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(19), P. 3860 - 3865

Published: Jan. 1, 2024

The aminophosphinoylation of alcohols with amines and H-phosphine oxides provides an efficient mild approach to access various α-aminoalkylphosphine in good yields tolerance functional groups using H 2 O as a clean solvent.

Language: Английский

Citations

4
Electrochemical synthesis of selenyl imidazo[2,1-b]thiazinones via three-component reactions DOI

Yuancheng Yue,

Ziren Chen, Fei Xue

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(20), P. 5813 - 5819

Published: Jan. 1, 2024

In this paper, we have developed an efficient strategy for the concise synthesis of diverse selenyl imidazo[2,1- b ]thiazinones via electrochemical oxidative three-component tandem reactions in absence transition metals, and oxidants.

Language: Английский

Citations

4
Electrochemical Synthesis of α-Thiocyanated/Methoxylated Ketones Using Enol Acetates DOI
Peng Zhang, Junwei Ma, Xuan Liu

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(23), P. 16122 - 16131

Published: Nov. 14, 2023

We have developed the synthesis of α-substituted ketone compounds with enol acetates in an electrochemical way. By using cheap NH4SCN and MeOH as radical sources, a series valuable α-thiocyanates/methoxy ketones were synthesized under mild electrolysis conditions acceptable yields diverse functional group compatibility. Additionally, scale-up experiment synthetic transformations reveal potential applications organic synthesis.

Language: Английский

Citations

9
Electrochemically Promoted Transesterification Reaction of Glycine Derivatives DOI
Xiaohu You,

Kejin Huang,

Shi‐Yi Zhuang

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 45(4), P. 1360 - 1360

Published: Jan. 1, 2025

Language: Английский

Citations

0
Phospha-Mannich reactions of phosphinous acids R 2 P–OH and their derivatives DOI
Д. В. Моисеев

Phosphorus, sulfur, and silicon and the related elements, Journal Year: 2023, Volume and Issue: 198(11), P. 867 - 923

Published: July 20, 2023

Secondary phosphine oxides R2P(O)H are a relatively stable tautomeric form of secondary phosphinous acids R2P–OH that with imine/iminium species, or their donors, compounds P(O)–Csp3–N linkage (the phospha-Mannich reaction). These can be referred to as (α-aminoalkyl)phosphine oxides, (α-phosphinoylalkyl)amines, P(O),N-acetals. Compared P–Csp3–N linkages P,N-acetals, products reactions involving phosphines R2PH, the is significantly more allows for many examples α-functionalized P(O),N-acetals and α-phosphinoylated N-heterocycles, whereas such P,N-acetals rare. Trivalent derivatives halides R2P–Hal, esters R2P–OR' (phosphinites), amides R2P–NR'2 (aminophosphines), phosphides R2P–PR'2 (biphosphines) also participate in Mannich-type mechanisms depending on reactants. The react (α-alkoxyalkyl)amines (N,O-acetals) (α-haloalkyl)amines (N,Hal-acetals), respectively, via Arbuzov-type intermediates rearranged into alkyl (Arbuzov rearrangement). Furthermore, unlike phosphines, less sensitive oxidation, imines/iminium species generated not only under conventional Mannich conditions, i.e., from N,E-acetals (E = OH, O, N, halogen, etc.), but also, example, by oxidation α-C-atom amines, alcohols aldehydes than amines.

Language: Английский

Citations

8