A Micellar Catalysis Strategy for Amidation of Alkynyl Bromides: Synthesis of Ynamides in Water

Yang, Yunqin; Meng, Xiangtai; Zhu, Baolong; Jia, Ying Ping; Cao, Xiaoji; Huang, Shenlin

doi:10.1002/ejoc.201801601

Cited by 18 publications

(9 citation statements)

References 69 publications

(16 reference statements)

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“…The surfactant, prepared by Yang et al, was shown to be highly effective in facilitating Cu-mediated amidation of alkynyl bromides under aqueous-micellar conditions, see Scheme 7 . 257 Normally, this type of transformation is conducted in dry solvents such as DMF, DMSO, or toluene at elevated temperatures. Side-reactions that can occur include homocoupling of alkynes to give 1,3-diynes, hydration of the diynes to furans, and hydration of ynamides to amides; 257 thus, the presence of water in the system is somewhat counterintuitive.…”

Section: Selection Of Alternative Solventsmentioning

confidence: 99%

“… 257 Normally, this type of transformation is conducted in dry solvents such as DMF, DMSO, or toluene at elevated temperatures. Side-reactions that can occur include homocoupling of alkynes to give 1,3-diynes, hydration of the diynes to furans, and hydration of ynamides to amides; 257 thus, the presence of water in the system is somewhat counterintuitive. However, the micellar conditions allow for smooth conversion of bromoalkynes to the corresponding ynamides.…”

Section: Selection Of Alternative Solventsmentioning

confidence: 99%

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Replacement of Less-Preferred Dipolar Aprotic and Ethereal Solvents in Synthetic Organic Chemistry with More Sustainable Alternatives

et al. 2022

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Dipolar aprotic and ethereal solvents comprise just over 40% of all organic solvents utilized in synthetic organic, medicinal, and process chemistry. Unfortunately, many of the common “go-to” solvents are considered to be “less-preferable” for a number of environmental, health, and safety (EHS) reasons such as toxicity, mutagenicity, carcinogenicity, or for practical handling reasons such as flammability and volatility. Recent legislative changes have initiated the implementation of restrictions on the use of many of the commonly employed dipolar aprotic solvents such as dimethylformamide (DMF) and N -methyl-2-pyrrolidinone (NMP), and for ethers such as 1,4-dioxane. Thus, with growing legislative, EHS, and societal pressures, the need to identify and implement the use of alternative solvents that are greener, safer, and more sustainable has never been greater. Within this review, the ubiquitous nature of dipolar aprotic and ethereal solvents is discussed with respect to the physicochemical properties that have made them so appealing to synthetic chemists. An overview of the current legislative restrictions being imposed on the use of dipolar aprotic and ethereal solvents is discussed. A variety of alternative, safer, and more sustainable solvents that have garnered attention over the past decade are then examined, and case studies and examples where less-preferable solvents have been successfully replaced with a safer and more sustainable alternative are highlighted. Finally, a general overview and guidance for solvent selection and replacement are included in the Supporting Information of this review.

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Section: Selection Of Alternative Solventsmentioning

confidence: 99%

Section: Selection Of Alternative Solventsmentioning

confidence: 99%

Replacement of Less-Preferred Dipolar Aprotic and Ethereal Solvents in Synthetic Organic Chemistry with More Sustainable Alternatives

et al. 2022

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“…For the preparation of sulfonamide compounds of type 1 and 2 (Figure 3), several procedures are present in the literature [54][55][56][57][58][59][60][61], and a few of them were also proposed recently in light of using more environmentally friendly green chemistry approaches [62][63][64][65][66].…”

Section: Synthesismentioning

confidence: 99%

In Silico Design, Synthesis, and Biological Evaluation of Anticancer Arylsulfonamide Endowed with Anti-Telomerase Activity

et al. 2022

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Telomerase, a reverse transcriptase enzyme involved in DNA synthesis, has a tangible role in tumor progression. Several studies have evidenced telomerase as a promising target for developing cancer therapeutics. The main reason is due to the overexpression of telomerase in cancer cells (85–90%) compared with normal cells where it is almost unexpressed. In this paper, we used a structure-based approach to design potential inhibitors of the telomerase active site. The MYSHAPE (Molecular dYnamics SHared PharmacophorE) approach and docking were used to screen an in-house library of 126 arylsulfonamide derivatives. Promising compounds were synthesized using classical and green methods. Compound 2C revealed an interesting IC50 (33 ± 4 µM) against the K-562 cell line compared with the known telomerase inhibitor BIBR1532 IC50 (208 ± 11 µM) with an SI ~10 compared to the BALB/3-T3 cell line. A 100 ns MD simulation of 2C in the telomerase active site evidenced Phe494 as the key residue as well as in BIBR1532. Each moiety of compound 2C was involved in key interactions with some residues of the active site: Arg557, Ile550, and Gly553. Compound 2C, as an arylsulfonamide derivative, is an interesting hit compound that deserves further investigation in terms of optimization of its structure to obtain more active telomerase inhibitors

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“…A variety of such nonionic benign by design surfactants is all considered PEGylated amphiphilic species, with or without a linker. TPGS-750-M [24], PQS [25], SPGS-550-M [26], Coolade [27], DAPGS-750-M [28], APGS-550-M [29], MC-1 [30], PTS [31], SMPS [32], BTBT-750-M, PiNAP-750-M [33], TPGlite [34], or PS-750-M [35] are some of the most studied excipients (Scheme 1). They have been demonstrated to be extremely versatile, most notably TPGS-750-M and PS-750-M, and shown to function as suitable surrogates to reprotoxic polar aprotic solvents, thus offering a real opportunity to phase out such solvents.…”

Section: Water Chemistry Enabled By Surfactantsmentioning

confidence: 99%

Organic synthesis in Aqueous Multiphase Systems — Challenges and opportunities ahead of us

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Ackermann

et al. 2021

Current Opinion in Colloid & Interface Science

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A Micellar Catalysis Strategy for Amidation of Alkynyl Bromides: Synthesis of Ynamides in Water

Cited by 18 publications

References 69 publications

Replacement of Less-Preferred Dipolar Aprotic and Ethereal Solvents in Synthetic Organic Chemistry with More Sustainable Alternatives

Replacement of Less-Preferred Dipolar Aprotic and Ethereal Solvents in Synthetic Organic Chemistry with More Sustainable Alternatives

In Silico Design, Synthesis, and Biological Evaluation of Anticancer Arylsulfonamide Endowed with Anti-Telomerase Activity

Organic synthesis in Aqueous Multiphase Systems — Challenges and opportunities ahead of us

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