☆ 4.4 Article

A Simple Synthesis of N-beta-Fmoc/Z-Amino Alkyl Thiols and their use in the Synthesis of N-beta-Fmoc/Z-Amino Alkyl Sulfonic Acids

SYNLETT (2010)

Journal

SYNLETT

Volume -, Issue 7, Pages 1037-1042

Publisher

GEORG THIEME VERLAG KG

DOI: 10.1055/s-0029-1219584

Keywords

alkyl iodides; thiourea; alkyl thiols; N-protected taurines; isothiuronium salts

Categories

Chemistry, Organic

Funding

Council of Scientific and Industrial Research, New Delhi, India [01(2323)/09/EMR-II]

Ask authors/readers for more resources

Protocol

Community support

Reagent

Community support

Abstract

A simple and efficient protocol for the synthesis of N-beta-Fmoc/Z-amino alkyl thiols is described. The approach uses sodium pyrosulfite-mediated hydrolysis of isothiouronium salts resulting from the reaction between N-protected aminoalkyl iodides and thiourea. N-Protected taurines were prepared through performic acid oxidation of the thiols and the products were further utilized for the synthesis of dipeptidosulfonamides.

Authors

I am an author on this paper

Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.4

Not enough ratings

Secondary Ratings

Novelty

-

Significance

-

Scientific rigor

-

Rate this paper

Recommended

Article Chemistry, Inorganic & Nuclear

Stepwise synthesis and catalysis in C-S cross-coupling of pyridine-functionalized N-heterocyclic carbene nickel(II) complexes by mechanochemistry

Xiaoxiao Cui, Xiujia Hao, Fang Guo

Summary: This paper describes the synthesis of three N-heterocyclic carbene complexes by stepwise grinding and their application as catalysts in C-S bond cross-coupling reactions.

DALTON TRANSACTIONS (2022)

Add to Collection

Article Chemistry, Organic

Abundant metal-catalyzed carbonylation of alkyl bromides and alkyl chlorides

Xing-Wei Gu, Xiao-Feng Wu

Summary: Transition metal-catalyzed carbonylation of alkyl halides is an efficient method for synthesizing aliphatic carbonyl-containing compounds. This paper discusses recent developments in the carbonylation reactions of alkyl bromides and chlorides catalyzed by abundant metals.

ORGANIC CHEMISTRY FRONTIERS (2023)

Add to Collection

Article Chemistry, Organic

Nickel-Catalyzed Reductive Thiolation of Unactivated Alkyl Bromides and Arenesulfonyl Cyanides

Fei Wang, Weidong Rao, Shun-Yi Wang

Summary: A practical and scalable method for the synthesis of unsymmetrical sulfides through cross-electrophile coupling between unactivated alkyl bromides and arenesulfonyl cyanides catalyzed by Ni(acac)(2) under reductive conditions has been developed. This catalytic strategy offers a complementary approach for the preparation of unsymmetrical alkyl-aryl sulfides with good functional group tolerance under mild conditions. It relies on readily available, unfunctionalized materials such as alkyl (pseudo)halides.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Add to Collection

Article Chemistry, Multidisciplinary

General electrochemical Minisci alkylation of N-heteroarenes with alkyl halides

Roberto del Rio-Rodriguez, Lorena Fragoso-Jarillo, Alberto F. Garrido-Castro, M. Carmen Maestro, Jose A. Fernandez-Salas, Jose Aleman

Summary: We report a general, facile, and environmentally friendly electrochemical method for the Minisci-type alkylation of N-heteroarenes using widely available alkyl halides as radical precursors. The method efficiently generates primary, secondary, and tertiary alkyl radicals, which can be coupled with a variety of N-heteroarenes. The method demonstrates high functional group tolerance and has been applied in the synthesis of biologically valuable building blocks.

CHEMICAL SCIENCE (2022)

Add to Collection

Article Chemistry, Organic

Deoxygenative C-S Bond Coupling with Sulfinates via Nickel/Photoredox Dual Catalysis

Shuai Zhong, Zhiwei Zhou, Feng Zhao, Guojiang Mao, Guo-Jun Deng, Huawen Huang

Summary: In this study, sulfinates were successfully used as sulfenylating reagents in C-S couplings through visible-light-induced photo/nickel dual catalysis under base- and external reductant-free conditions. The method showed high selectivity and tolerance towards various functionalities.

ORGANIC LETTERS (2022)

Add to Collection

Article Chemistry, Organic

Metallaphotoredox-Catalyzed C-S Cross-Coupling between Heteroaryl Bromides and α-Thioacetic Acids to Access Biaryl Thioethers

Alec H. Christian

Summary: The metallaphotoredox-catalyzed C-S cross-coupling allows for the formation of biaryl thioethers from heteroaryl bromides and alpha-thioacetic acids. This method facilitates cross-coupling between building blocks containing reactive functional groups, nitrogen heterocycles, and pharmaceutically relevant scaffolds. Mechanistic experiments show a unique pathway for the C-S cross-coupling to occur.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Add to Collection

Article Chemistry, Organic

Difluoromethylation of Alkyl Bromides and Iodides with TMSCF2H

Haiwei Zhao, Changhui Lu, Simon Herbert, Wei Zhang, Qilong Shen

Summary: Two protocols for direct difluoromethylation of alkyl bromides and iodides are introduced, utilizing different catalysts and activators. Preliminary mechanistic studies suggest that the synergistic Pd/Cu-catalyzed difluoromethylation of alkyl bromides likely proceeds via a Pd(I)/Pd(III) catalytic cycle.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Add to Collection

Article Chemistry, Organic

Visible-Light-Mediated Alkylation of Thiophenols via Electron Donor-Acceptor Complexes Formed between Two Reactants

Yi-Ping Cai, Fang-Yuan Nie, Qin-Hua Song

Summary: A metal-free, photocatalyst-free photochemical system has been developed for the direct alkylation of thiophenols using electron donor-acceptor complexes. These complexes have a broad range of visible-light absorption and can effectively trigger the reaction under sunlight.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Add to Collection

Article Chemistry, Organic

Regioselective Asymmetric Alkynylation of N-Alkyl Pyridiniums

Thiago A. Grigolo, Ariana R. Subhit, Joel M. Smith

Summary: This novel method allows for asymmetric addition of alkynyl nucleophiles to N-alkylpyridinium electrophiles, with complete control over regiochemical and stereochemical properties. The utility of this transformation is demonstrated through a concise, dearomative, and asymmetric synthesis of a natural acetylcholine esterase inhibitor, (+)-lupinine.

ORGANIC LETTERS (2021)

Add to Collection

Article Multidisciplinary Sciences

Iridium-catalyzed direct asymmetric reductive amination utilizing primary alkyl amines as the N-sources

Zitong Wu, Wenji Wang, Haodong Guo, Guorui Gao, Haizhou Huang, Mingxin Chang

Summary: Direct asymmetric reductive amination is an efficient method for obtaining chiral amines. In this study, the authors demonstrate how primary alkyl amines can undergo this transformation in the presence of an iridium catalyst with sterically tuneable chiral phosphoramidite ligands, leading to the synthesis of pharmaceutical compounds.

NATURE COMMUNICATIONS (2022)

Add to Collection

Article Chemistry, Organic

Site-selective C-H difunctionalization of N-alkyl activated azaarenes via the synergistic catalysis of graphene oxide and visible light

De-Hao Duan, Hai-Ping He, Wei-Yi Ding, Dong-Cheng Yi, Ying-Zhen Lai, Ai-Qiong Huang, Jie Liu, Wen-Le Wu, Xiang-Jun Peng

Summary: This article introduces a strategy for site-selective reactions on N-alkyl activated azaarenes using graphene oxide as a heterogeneous cocatalyst, which is induced by visible light. The site-selectivity can be switched from C4 to C2 by changing the base and solvent. It was also found that the resulting compounds exhibit antitumor activity against HeLa cells, and a certain organocatalyst has the ability to tune emission and quantum yields in optical materials.

ORGANIC CHEMISTRY FRONTIERS (2023)

Add to Collection

Article Chemistry, Multidisciplinary

Heterocyclic group transfer reactions with I(iii) N-HVI reagents: access to N-alkyl(heteroaryl)onium salts via olefin aminolactonization

Anthony F. Tierno, Jennifer C. Walters, Andres Vazquez-Lopez, Xiao Xiao, Sarah E. Wengryniuk

Summary: This study utilizes N-HVI reagents as heterocyclic group transfer reagents to provide a broad scope of N-alkyl(heteroaryl)onium salts via aminolactonization of alkenoic acids, showcasing a novel method for their synthesis.

CHEMICAL SCIENCE (2021)

Add to Collection

Article Chemistry, Organic

In Situ Alkyl Radical Recycling-Driven Decoupled Electrophotochemical Deamination

Kui Wang, Xiaoyu Liu, Siyu Yang, Yan Tian, Mingyang Zhou, Jianhua Zhou, Xiaofei Jia, Baoying Li, Siyuan Liu, Jianbin Chen

Summary: Molecular electrophotocatalysis is a powerful strategy for sustainable synthesis, and has been applied in a versatile electrophotocatalytic deaminative alkylation approach. The key point lies in the in situ recycling of alkyl radicals, and the method has also been successfully applied in ligand modification and late-stage functionalization of pharmaceuticals.

ORGANIC LETTERS (2022)

Add to Collection

Article Chemistry, Organic

Visible-Light-Induced C(sp2)-C(sp3) Cross-Dehydrogenative-Coupling Reaction of N-Heterocycles with N-Alkyl-N-methylanilines under Mild Conditions

Hong-Yu Zhang, Jianjun Chen, Cong-Cong Lu, Ya-Ping Han, Yuecheng Zhang, Jiquan Zhao

Summary: This study describes a cross-dehydrogenative-coupling reaction using visible light and air at room temperature to synthesize aminomethyl-substituted N-heterocycles, providing an efficient, environmentally friendly, and convenient method.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Add to Collection

Article Chemistry, Inorganic & Nuclear

Indirect photolysis of cysteine and thiourea in the aquatic environment

Gheorghe Duca, Angela Lis, Viorica Gladchi, Sergey Travin

Summary: The aim of this research is to study the photochemical transformations of thiourea (TU) and cysteine (Cys) in aqueous solutions and evaluate their roles in aquatic systems. Both TU and Cys were subjected to indirect photolysis with OH radicals generated by the photodissociation of hydrogen peroxide under different light sources. The indirect photolysis rates of TU and Cys were found to depend on the substrate's chemical nature, initial concentrations, and H2O2. TU and Cys undergo photochemical transformations through complex radical mechanisms.

INORGANICA CHIMICA ACTA (2023)

Add to Collection

No Data Available

No Data Available

© Peeref 2019-2024. All rights reserved.