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SYNTHESIS-STUTTGART · 2013 ·Vol. 45 ·期 16 ·2234-2240 · IF 2.5

Gram-Scale Ketone Synthesis by Direct Reductive Coupling of Alkyl Iodides with Acid Chlorides

Wenbin Lu,Zhuye Liang,Yuwei Zhang,Fan Wu,Qun Qian,Hegui Gong

Alkyl aryl ketones were prepared on a gram scale by the nickel-catalyzed reductive coupling of alkyl iodides with aroyl chlorides. When scaled up 30-fold, this reaction shows a comparable coupling efficiency to the previously reported reaction performed under small-scale conditions. The mild and convenient reaction conditions show excellent tolerance to a range of functional groups and provide the ketones in good to excellent yields.

研究领域: 有机化学 · 合成化学
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SYNTHESIS-STUTTGART · 2013 ·Vol. 45 ·期 24 ·3387-3391 · IF 2.5

Copper/Imidazolium/TEMPO-Catalyzed Aerobic Oxidation of Benzylic Alcohols­ in Water

Congyan Chen,Bo Liu,Wanzhi Chen

Various imidazolium salts bearing hydrophilic groups were prepared that reacted with copper powder to afford water-soluble­ copper complexes of N-heterocyclic carbenes. These copper complexes can catalyze the selective oxidation of benzyl alcohols to the corresponding aldehydes in water at room temperature without the need for a base.

研究领域: 有机化学 · 催化化学 · 绿色化学
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SYNTHESIS-STUTTGART · 2022 ·Vol. 54 ·期 18 ·3977-3988 · IF 2.969

Metal-Free Thiolation and Hydroxylation of CF3-Substituted Alkenes: A Practical Method to Synthesize Trifluoromethyl Tertiary Alcohols

Jiapan Niu,Bowen Liu,Chun Zhang

A novel and practical method to synthesize trifluoromethyl tertiary alcohols has been developed. Under mild reaction conditions, the present reaction could be compatible with a wide range of functional groups. Moreover, the performance of gram-scale reaction and further transformations illustrated the good potential utility of the present chemistry. Furthermore, the radical process of this reaction has been proved by mechanistic studies.

研究领域: 有机化学 · 药物化学 · 氟化学 · 合成方法学
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SYNTHESIS-STUTTGART · 2016 ·Vol. 48 ·期 17 ·2829-2836 · IF 2.652

Nickel-Catalyzed Reductive Cross-Coupling of Benzyl Halides with Aryl Halides

Qingchen Zhang,Xuan Wang,Qun Qian,Hegui Gong

Systematic studies of the coupling of benzylic with aryl halides are presented. The optimized reaction conditions for electron-deficient­ aryl halides cannot be applied to the electron-rich or neutral counterparts, and vice versa. The excellent functional group tolerance and broad substrate scope may enable the current work to be useful for the construction of diaryl methane products.

研究领域: 有机化学 · 合成化学 · 过渡金属催化
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SYNTHESIS-STUTTGART · 2019 ·Vol. 51 ·期 17 ·3221-3230 · IF 2.867

One-Pot Synthesis of Polysubstituted Imidazoles Based on Pd(OAc)2/Ce(SO4)2/Bi(NO3)3 Trimetallic Cascade of Decarboxylation/Wacker-Type Oxidation/Debus–Radziszewski Reaction

Wei Sun,Mingjuan Zhang,Peilang Li,Yiqun Li

A novel and highly efficient one-pot synthesis of polysubstituted imidazoles from α-hydroxyphenylacetic acids, diphenylacetylene, and amines has been achieved by Pd(OAc)2/Ce(SO4)2/Bi(NO3)3 trimetallic catalytic system. A series of control experiments showed that this overall reaction occurs through a one-pot cascade process combining the steps of decarboxylation of α-hydroxyphenylacetic acids, Wacker-type oxidation of diphenylacetylene, and Debus–Radziszewski annulation of aryl aldehydes and benzil generated in situ, as well as amines. This reaction represents a novel multicomponent reaction using α-hydroxyphenylacetic acids and diphenylacetylene as sources of aryl aldehydes and a β-diketone. This process exhibits a broad substrate scope and a good functional group tolerance to assemble the corresponding polysubstituted imidazoles in excellent yields (72–88%) under mild conditions.

研究领域: 有机化学 · 催化化学 · 药物化学 · 合成方法学 · 杂环化学
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SYNTHESIS-STUTTGART · 2022 ·Vol. 54 ·期 09 ·2251-2257 · IF 2.969

Nickel-Catalyzed Reductive Cross-Coupling of Oxalates Derived from α-Hydroxy Carbonyls with Vinyl Bromides

Cheng Ye,Weiqi Tong,Fan Wu

A nickel-catalyzed cross-electrophile coupling is disclosed in which a range of vinyl bromides were utilized as electrophiles with oxalates derived from α-hydroxy carbonyls as precursors to carbonyl radical coupling partners. This method is compatible with a broad range of functional groups, providing a complementary solution for the construction of β,γ-unsaturated carbonyl compounds.

研究领域: 有机化学 · 合成化学 · 催化
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PLANTA MEDICA · 2014 ·Vol. 80 ·期 11 ·925-930 · IF 2.339

Cytotoxic and Antimicrobial Flavonoids from Cryptocarya concinna

Wei Huang,Wen-Jing Zhang,Yi-Qing Cheng,Rong Jiang,Wei Wei,Chao-Jun Chen,Gang Wang,Rui-Hua Jiao,Ren-Xiang Tan,Hui-Ming Ge

Five new flavonoids, cryptoconones A–E (1–5), along with six known compounds (6–11), were isolated from the stems of Cryptocarya concinna. The structures of these compounds were elucidated on the basis of spectroscopic data interpretation, and the absolute configurations were determined via circular dichroism spectra and X-ray crystal analysis. The cytotoxic and antimicrobial activities of these compounds were also evaluated. Compounds 9 and 10 exhibited moderate cytotoxic activities against HCT116, HT-29, SW480, and MDA-MB-231 cell lines with IC50 values ranging from 6.25 to 9.35 µM. Compounds 8 and 11 exhibited antimicrobial activity against Fusarium moniliforme and Botrytis cinerea, respectively, with the same minimum inhibitory concentration of 5 µg/mL.

研究领域: 药物学 · 药物化学 · 微生物学 · 肿瘤学
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SYNLETT · 2018 ·Vol. 29 ·期 09 ·1244-1248 · IF 2.369

PPh3-Mediated [3+2] Cycloaddition Reaction between Bis-Substituted Allenoate and N-Tosylaldimines to Construct 2-Pyrrolines

Xiangwen Kong,Lihua Liu,Siqin Luo,Shilu Fan,Haisheng Qian,Hua Xiao

A triphenylphosphine-promoted [3+2] cycloaddition of α,γ-bis-substituted allenoates and N-tosylaldimines followed by alkene isomerization was disclosed, affording a series of functionalized 2-pyrroline derivatives in moderate chemical yields with random diastereoselectivities.

研究领域: 有机化学 · 药物化学 · 合成方法学 · 杂环化学
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SYNTHESIS-STUTTGART · 2015 ·Vol. 48 ·期 02 ·231-237 · IF 2.689

Phosphorous Acid Promoted Hydration–Condensation of Aromatic Alkynes with Aldehydes Affording Chalcones in an Oil/Water Two-Phase System

Yongbo Zhou,Zhongwen Li,Xiao Yang,Xiulin Chen,Mei Li,Tieqiao Chen,Shuang-Feng Yin

A simple and environmentally benign method was developed for the synthesis of chalcones in high to excellent yields by a phosphorous acid promoted alkyne–aldehyde hydration–condensation in an oil/water two-phase system. The method is the first efficient protocol for the preparation of chalcones that is mediated by a simple Brønsted acid in a two-phase system.

研究领域: 有机化学 · 绿色化学
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SYNTHESIS-STUTTGART · 2022 ·Vol. 54 ·期 09 ·2258-2266 · IF 2.969

DMSO-Mediated Difunctionalization of Electron-Deficient Olefins to Access β-Hydroxysulfides with High Chemoselectivity

Bao Gao,Xiaojun Liu,Qian Yan,Ruiting Yang,Tao Jiang,Xiuli Zhang

A novel and convenient method for the highly chemoselective synthesis of β-hydroxysulfides mediated by DMSO is reported. This eco-friendly reaction was amenable to a broad range of substrates and provided the desired β-hydroxysulfides in moderate to good yields with high selectivity via radical process. Moreover, several pharmaceutical and bioactive molecules were also suitable substrates for this reaction conditions to afford the targeted products in good yields.

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SynOpen · 2023 ·Vol. 07 ·期 04 ·486-490 · IF 2.5

Synthesis and Characterization of an Eight-Membered Heterocyclic 1,3,5,7-Tetra(3-pyridyl)-1,3,5,7-tetrazacyclooctane

Li Li,Guo-Liang Dai,Xue Hua Zhu,Lei Yu,Hai Yan Li

N,N′-Bis(3-pyridyl)methanediamine was prepared by treating 3-aminopyridine with formaldehyde in acetonitrile. By treating it with formaldehyde, the eight-membered heterocyclic ring compound 1,3,5,7-tetra(3-pyridyl)-1,3,5,7-tetrazacyclooctane was prepared. This could occur in a two-step manner in a [3+1+3+1] cycloaddition reaction. The compounds were characterized by X-ray crystallography, 1H and 13C NMR spectroscopy, and mass spectrometry. The powder XRD pattern of 1,3,5,7-tetra(3-pyridyl)-1,3,5,7-tetrazacyclooctane was also determined and revealed an uncommon twist-crown conformation, which was further confirmed by DFT calculations.

CAS / MDL: 462-08-8
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SYNTHESIS-STUTTGART · 2019 ·Vol. 51 ·期 23 ·4425-4433 · IF 2.867

Nitroacenaphthene as a New Photocatalyst for the Synthesis of Sulfonyl Amidines

Yong Jian,Ming Chen,Chao Yang,Wujiong Xia

A small molecule, namely nitroacenaphthene, is reported for the first time as a recyclable visible-light photocatalyst for the construction of the C=N bond from sulfonyl azides and amines. This scalable, site-selective protocol provides a convenient way to access various sulfonyl amidines under mild conditions. Two reaction pathways are proposed, according to different transformation patterns.

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