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Search for "alcohols" in Full Text gives 757 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Palladium-catalyzed three-component radical-polar crossover carboamination of 1,3-dienes or allenes with diazo esters and amines

  • Geng-Xin Liu,
  • Xiao-Ting Jie,
  • Ge-Jun Niu,
  • Li-Sheng Yang,
  • Xing-Lin Li,
  • Jian Luo and
  • Wen-Hao Hu

Beilstein J. Org. Chem. 2024, 20, 661–671, doi:10.3762/bjoc.20.59

Graphical Abstract
  • products 4a and 6a (Scheme 6). Both model reactions with diene 2a and allene 5a were proven to be easily scalable without further conditions optimization, delivering unsaturated γ- and ε-AA derivatives 4a and 6a in good yields. Starting from the unsaturated ε-AA derivative 4a, unsaturated ζ-amino alcohols
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Published 27 Mar 2024

Entry to new spiroheterocycles via tandem Rh(II)-catalyzed O–H insertion/base-promoted cyclization involving diazoarylidene succinimides

  • Alexander Yanovich,
  • Anastasia Vepreva,
  • Ksenia Malkova,
  • Grigory Kantin and
  • Dmitry Dar’in

Beilstein J. Org. Chem. 2024, 20, 561–569, doi:10.3762/bjoc.20.48

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  • alcohols, followed by base-promoted cyclization to afford the target spirocyclic compounds in good to high yields. Keywords: diazoarylidene succinimides; intramolecular cyclization; rhodium(II) carbene O–H insertion; spirocycles; Introduction Spirocyclic motifs have emerged as auspicious frameworks for
  • from each of the bromo-substituted alcohols used by us have two main pathways of transformation under the action of base: 1) exo-tet cyclization with substitution of the bromine atom and formation of the spirocycle, and 2) migration of the exocyclic double C=C bond into the imide cycle (the process is
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Published 11 Mar 2024

Ligand effects, solvent cooperation, and large kinetic solvent deuterium isotope effects in gold(I)-catalyzed intramolecular alkene hydroamination

  • Ruichen Lan,
  • Brock Yager,
  • Yoonsun Jee,
  • Cynthia S. Day and
  • Amanda C. Jones

Beilstein J. Org. Chem. 2024, 20, 479–496, doi:10.3762/bjoc.20.43

Graphical Abstract
  • Since the seminal 1998 report by Teles et al. on the gold(I)-catalyzed addition of alcohols to alkynes [1], a multitude of gold-catalyzed reactions have been reported. Great successes in mechanistic analysis and synthetic methods have been achieved for allene and alkyne activation, while the activation
  • effect of MeOH co-solvent on the 1a → 3a transformation was due to its role as a hydrogen bonding donor (proton source), or due to its role as a hydrogen bonding acceptor (Lewis base) [44]. To this end, we examined the impact of different alcohols (varied acidity and polarity) and different non-protic
  • Lewis bases as additive to the bulk CH2Cl2 solvent (Figure 6) and compared them to the baseline rate in the absence of additive. The rates of formation of 3a are mildly sensitive to alcohol structure with MeOH outperforming EtOH and propanol. For the set of linear alcohols, the shorter the chain, the
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Published 29 Feb 2024

Nucleophilic functionalization of thianthrenium salts under basic conditions

  • Xinting Fan,
  • Duo Zhang,
  • Xiangchuan Xiu,
  • Bin Xu,
  • Yu Yuan,
  • Feng Chen and
  • Pan Gao

Beilstein J. Org. Chem. 2024, 20, 257–263, doi:10.3762/bjoc.20.26

Graphical Abstract
  • -metal-catalyzed cross-coupling [32][33] and aminofunctionalization [34] of alkenes were achieved, benefiting from the unique reactivity of organothianthrenium species that are generated through the reaction of alkenes and thianthrene sulfoxide (TT=O) or thianthrene (TT) (Scheme 1b). Alcohols are widely
  • [35], it is still a great challenge to transform alcohols into valuable chemicals [36][37][38]. A recent study by Shi and co-workers has successfully converted alcohols into thianthrenium salts, enabling the transformation of the hydroxy (OH) group into various functional groups via the photoassisted
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Published 08 Feb 2024

A series of perylene diimide cathode interlayer materials for green solvent processing in conventional organic photovoltaics

  • Kathryn M. Wolfe,
  • Shahidul Alam,
  • Eva German,
  • Fahad N. Alduayji,
  • Maryam Alqurashi,
  • Frédéric Laquai and
  • Gregory C. Welch

Beilstein J. Org. Chem. 2023, 19, 1620–1629, doi:10.3762/bjoc.19.119

Graphical Abstract
  • impact of morphological changes on device performance [18][19]. With respect to the latter, we have introduced ethyl acetate as a suitable green solvent to process CILs onto high performance BHJs (e.g., PM6:Y6). Most CILs have been processed from alcohols as to not damage the underlying hydrophobic BHJ
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Published 26 Oct 2023

Radical chemistry in polymer science: an overview and recent advances

  • Zixiao Wang,
  • Feichen Cui,
  • Yang Sui and
  • Jiajun Yan

Beilstein J. Org. Chem. 2023, 19, 1580–1603, doi:10.3762/bjoc.19.116

Graphical Abstract
  • of surfactants, which are also called emulsifiers within the first few minutes [26]. Emulsifiers such as sodium lauryl sulfate, sodium or potassium salts of fatty acids (soaps), salts of alkylbenzene sulfonates, and O-polyoxyethyleneated long-chain alcohols are used to change the two incompatible
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Published 18 Oct 2023
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  • ], amino alcohols [10], and amino acids [11] have been studied due to their potential applications in supramolecular chemistry, drug delivery, and molecular recognition. The complexation of R[4]A with amines is based on the formation of hydrogen bonds between the hydroxy groups of the resorcinol units and
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Published 29 Sep 2023

N-Sulfenylsuccinimide/phthalimide: an alternative sulfenylating reagent in organic transformations

  • Fatemeh Doraghi,
  • Seyedeh Pegah Aledavoud,
  • Mehdi Ghanbarlou,
  • Bagher Larijani and
  • Mohammad Mahdavi

Beilstein J. Org. Chem. 2023, 19, 1471–1502, doi:10.3762/bjoc.19.106

Graphical Abstract
  • ]. Moreover, sulfenylation of ketoximes and secondary nitro compounds toward N-arenesulfenyl ketimines occurred by applying N-(phenylthio)phthalimide [69]. In 2011, Shi et al. developed a method for the sulfenylation of unsaturated alcohols 86 by N-(benzylthio)succinimide 1 access to tetrahydrofurans 87 and
  • presence of TMSOTf. Catalyst-free sulfenylation by N-(sulfenyl)succinimides/phthalimides In 2015, oxysulfenylation of styrene derivatives 9 utilizing 1-(arylthio)pyrrolidine-2,5-diones 1 and alkyl/benzyl alcohols 86 toward β-alkoxy sulfides was developed by Fu et al. (Scheme 65) [95]. In this metal-free
  • of the product, while benzoyl peroxide (BPO) gave a low yield. Various nucleophiles 161, including ammonia, alkylamines, hydrazines, alcohols and alkoxides, indole, N-alkylpyrrole, N-substituted anilines, PhSH, and PhMgBr worked well under these conditions. Asymmetric thiolation of 4-substituted
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Published 27 Sep 2023

Functions of enzyme domains in 2-methylisoborneol biosynthesis and enzymatic synthesis of non-natural analogs

  • Binbin Gu,
  • Lin-Fu Liang and
  • Jeroen S. Dickschat

Beilstein J. Org. Chem. 2023, 19, 1452–1459, doi:10.3762/bjoc.19.104

Graphical Abstract
  • obtained through standard phosphorylation of the corresponding known alcohols [35][36][37]. In a first screening, these derivatives were tested in all possible combinations in small scale reactions (0.3 mg of each substrate) with FPPS. The results were investigated through dephosphorylation with calf
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Published 22 Sep 2023

α-(Aminomethyl)acrylates as acceptors in radical–polar crossover 1,4-additions of dialkylzincs: insights into enolate formation and trapping

  • Angel Palillero-Cisneros,
  • Paola G. Gordillo-Guerra,
  • Fernando García-Alvarez,
  • Olivier Jackowski,
  • Franck Ferreira,
  • Fabrice Chemla,
  • Joel L. Terán and
  • Alejandro Perez-Luna

Beilstein J. Org. Chem. 2023, 19, 1443–1451, doi:10.3762/bjoc.19.103

Graphical Abstract
  • stereocenter. α-(Aminomethyl)acrylates 5–7 reacted smoothly at −33 °C within 2 h with Et2Zn in the presence of cyclohexanone to afford amino alcohols 18–20 in quite good yields (63–68%). Even better yields were obtained with enoates 8a and 8b both with cyclohexanone and acetone as carbonyl partners. Starting
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Published 21 Sep 2023

Application of N-heterocyclic carbene–Cu(I) complexes as catalysts in organic synthesis: a review

  • Nosheen Beig,
  • Varsha Goyal and
  • Raj K. Bansal

Beilstein J. Org. Chem. 2023, 19, 1408–1442, doi:10.3762/bjoc.19.102

Graphical Abstract
  • of the NHC–CuCl-catalyzed hydroborylation of propargylic alcohols (157, R = H) and ethers (157, R = aryl, alkyl) was dependent on the size of the NHC [85] (Scheme 62). Interestingly, the application of the catalyst 158 comprising a bulkier NHC preponderantly led to the sterically crowded α
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Published 20 Sep 2023

Functional characterisation of twelve terpene synthases from actinobacteria

  • Anuj K. Chhalodia,
  • Houchao Xu,
  • Georges B. Tabekoueng,
  • Binbin Gu,
  • Kizerbo A. Taizoumbe,
  • Lukas Lauterbach and
  • Jeroen S. Dickschat

Beilstein J. Org. Chem. 2023, 19, 1386–1398, doi:10.3762/bjoc.19.100

Graphical Abstract
  • ; biosynthesis; enzymes; NMR spectroscopy; terpenes; Introduction Terpene synthases are remarkable enzymes that can convert acyclic and achiral oligoprenyl pyrophosphates into terpene hydrocarbons or alcohols of high structural complexity. These enzymatic reactions are initiated by ionisation of the substrate
  • in sesquiterpene biosynthesis that can be reactivated by reprotonation for a second cyclisation to eudesmane (6,6-bicyclic) or guaiane (7,5-bicyclic) sesquiterpene hydrocarbons or alcohols, respectively [46][47]. Starting from 26, such a protonation induced cyclisation can lead to C that is the
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Published 15 Sep 2023

Visible-light-induced nickel-catalyzed α-hydroxytrifluoroethylation of alkyl carboxylic acids: Access to trifluoromethyl alkyl acyloins

  • Feng Chen,
  • Xiu-Hua Xu,
  • Zeng-Hao Chen,
  • Yue Chen and
  • Feng-Ling Qing

Beilstein J. Org. Chem. 2023, 19, 1372–1378, doi:10.3762/bjoc.19.98

Graphical Abstract
  • nickel-catalyzed coupling of aryl bromides with an α-hydroxytrifluoroethyl radical for the synthesis of trifluoromethyl aryl alcohols [39]. Encouraged by this work, we envisioned that the nickel-catalyzed coupling of carboxylic acids-derived acyl electrophiles with an α-hydroxytrifluoroethyl radical
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Published 11 Sep 2023

Synthesis of ether lipids: natural compounds and analogues

  • Marco Antônio G. B. Gomes,
  • Alicia Bauduin,
  • Chloé Le Roux,
  • Romain Fouinneteau,
  • Wilfried Berthe,
  • Mathieu Berchel,
  • Hélène Couthon and
  • Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2023, 19, 1299–1369, doi:10.3762/bjoc.19.96

Graphical Abstract
  • protection was not regioselective (a mixture of primary and secondary protected alcohols was formed). The acylation of the secondary alcohol was then achieved with acetic anhydride in the presence of pyridine. Then, the deprotection of the trityl moiety of compound 12.4 by catalytic hydrogenation failed
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Published 08 Sep 2023

Metal catalyst-free N-allylation/alkylation of imidazole and benzimidazole with Morita–Baylis–Hillman (MBH) alcohols and acetates

  • Olfa Mhasni,
  • Jalloul Bouajila and
  • Farhat Rezgui

Beilstein J. Org. Chem. 2023, 19, 1251–1258, doi:10.3762/bjoc.19.93

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  • Toulouse, France University of Tunis El Manar, Laboratory of Organic Chemistry, Faculty of Sciences, Campus, 2092 Tunis, Tunisia 10.3762/bjoc.19.93 Abstract A highly α-regioselective N-nucleophilic allylic substitution of cyclic MBH alcohols and acetates with imidazole or benzimidazole, in toluene at
  • reflux with an azeotropic distillation, was successfully carried out with no catalysts or additives, affording the corresponding N-substituted imidazole derivatives in good yields. On the other hand, in refluxing toluene or methanol, the aza-Michael addition of imidazole onto acyclic MBH alcohols was
  • bifonazole have become well-established drugs for the treatment of numerous mycotic infections (Figure 1) [9][10]. Therefore, the development of new methods for the preparation of such compounds is highly required. The MBH acetates, instead of the corresponding alcohols, have been extensively used as
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Published 01 Sep 2023
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  • body of work using simple alcohols as a proton and electron source in electrochemical hydrogenations [43]. This could also evolve into an extension of artificial photosynthesis if the alcohols used as donors are generated by artificial or natural photosynthesis (i.e., photosynthetic bacteria). NADH and
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Published 08 Aug 2023

Selective and scalable oxygenation of heteroatoms using the elements of nature: air, water, and light

  • Damiano Diprima,
  • Hannes Gemoets,
  • Stefano Bonciolini and
  • Koen Van Aken

Beilstein J. Org. Chem. 2023, 19, 1146–1154, doi:10.3762/bjoc.19.82

Graphical Abstract
  • oxygen- or radical-sensitive functionalities (i.e., an amino (2w) or nitro group (2x)). On the other hand, oxidizable groups, such as alcohols (2e), and halogens, such as such as chloro and fluoro on the aromatic ring (2i ,2j, 2k), were well tolerated. However, the presence of a iodo group (2v
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Published 31 Jul 2023

Photoredox catalysis harvesting multiple photon or electrochemical energies

  • Mattia Lepori,
  • Simon Schmid and
  • Joshua P. Barham

Beilstein J. Org. Chem. 2023, 19, 1055–1145, doi:10.3762/bjoc.19.81

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Published 28 Jul 2023

Five new sesquiterpenoids from agarwood of Aquilaria sinensis

  • Hong Zhou,
  • Xu-Yang Li,
  • Hong-Bin Fang,
  • He-Zhong Jiang and
  • Yong-Xian Cheng

Beilstein J. Org. Chem. 2023, 19, 998–1007, doi:10.3762/bjoc.19.75

Graphical Abstract
  • present study, it was described that skeletons with 1°-alcohols and/or acid groups suppress activity, which was consistent with the A. sinensis literatures that 1°-alcohols and/or acid groups suppress activity [25][27], and concluded that eudesmane-type sesquiterpenes constructed with aldehyde groups are
  • more active than alcohols or acids. Conclusion In summary, five new eudesmane-type sesquiterpenes compounds (1–5) and five known compounds (6–10) were isolated from agarwood of A. sinensis. The discovery of these new compounds enriches the structural diversity and complexity of sesquiterpenes derived
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Published 30 Jun 2023

Synthesis of tetrahydrofuro[3,2-c]pyridines via Pictet–Spengler reaction

  • Elena Y. Mendogralo and
  • Maxim G. Uchuskin

Beilstein J. Org. Chem. 2023, 19, 991–997, doi:10.3762/bjoc.19.74

Graphical Abstract
  • the use of 3-substituted furans. For example, the intramolecular Friedel–Crafts alkylation reaction (Scheme 1a) of alcohols [9][10][11], alkenes [12] or acetylenes [13] affords the desired tetrahydrofuro[3,2-c]pyridines. A related method is based on a Au(I)-catalyzed domino sequence dearomatization
  • ][18] was described (Scheme 1c). The most studied variation of this cyclization is based on the generation of an acyliminium cation from the corresponding alcohols [19][20][21][22][23] or alkenes [24][25][26][27][28][29], subsequent attack of furan ring and the formation of annulated tetrahydrofuro[3,2
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Published 30 Jun 2023

Clauson–Kaas pyrrole synthesis using diverse catalysts: a transition from conventional to greener approach

  • Dileep Kumar Singh and
  • Rajesh Kumar

Beilstein J. Org. Chem. 2023, 19, 928–955, doi:10.3762/bjoc.19.71

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  • P2O5 under toluene at 110 °C. Since phosphorus pentoxide gives phosphoric acid esters upon reaction with alcohols and also has less acidic character, the authors hypothesized that it might be a good choice for the conversion of amines 10 into their corresponding pyrroles. The results were according to
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Published 27 Jun 2023

Photoredox catalysis enabling decarboxylative radical cyclization of γ,γ-dimethylallyltryptophan (DMAT) derivatives: formal synthesis of 6,7-secoagroclavine

  • Alessio Regni,
  • Francesca Bartoccini and
  • Giovanni Piersanti

Beilstein J. Org. Chem. 2023, 19, 918–927, doi:10.3762/bjoc.19.70

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  • intramolecular 7-endo-trig ring closure) may well be the thermodynamic product based on the more stabilized benzylic radical that is produced [101]. As largely reported in the literature [102][103], radicals generated next to alcohols do not normally undergo β-elimination to give alkene/carbon–carbon double-bond
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Published 26 Jun 2023

Synthesis of aliphatic nitriles from cyclobutanone oxime mediated by sulfuryl fluoride (SO2F2)

  • Xian-Lin Chen and
  • Hua-Li Qin

Beilstein J. Org. Chem. 2023, 19, 901–908, doi:10.3762/bjoc.19.68

Graphical Abstract
  • activated intermediates for a variety of transformations [46][47][48][49][50][51][52][53][54][55][56][57][58]. Lately, we discovered the SO2F2-mediated transformation of primary alcohols to nitriles, involving an aldoxime sulfonyl ester intermediate (Scheme 2c) [59]. Drawing inspiration from these excellent
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Published 22 Jun 2023

Sulfate radical anion-induced benzylic oxidation of N-(arylsulfonyl)benzylamines to N-arylsulfonylimines

  • Joydev K. Laha,
  • Pankaj Gupta and
  • Amitava Hazra

Beilstein J. Org. Chem. 2023, 19, 771–777, doi:10.3762/bjoc.19.57

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  • -dehydrative reaction of aldehydes with isocyanate analogs ([3] and references therein) (Scheme 1b) and an oxidative reaction of primary benzylic alcohols with sulfonamides or chloramine-T ([3] and references therein), and although they are elegant, they use substrates that are not readily accessible or toxic
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Published 05 Jun 2023

Honeycomb reactor: a promising device for streamlining aerobic oxidation under continuous-flow conditions

  • Masahiro Hosoya,
  • Yusuke Saito and
  • Yousuke Horiuchi

Beilstein J. Org. Chem. 2023, 19, 752–763, doi:10.3762/bjoc.19.55

Graphical Abstract
  • structure raised the mixing efficiency of a gas–liquid reaction system, and it effectively accelerated the aerobic oxidation of benzyl alcohols to benzaldehydes under continuous-flow conditions. This reactor is a promising device for streamlining aerobic oxidation with high process safety because it is a
  • closed system. Keywords: aerobic oxidation; benzaldehydes; benzyl alcohols; homogeneous catalyst; honeycomb reactor; Introduction Oxidation plays a key role in synthesizing highly functionalized molecules [1][2]. While Jones oxidation [3] and oxidation using KMnO4 [4] are classical and powerful methods
  • ], and its screening results can be transferred to obtain a wide variety of benzaldehydes from benzyl alcohols. The screening was conducted under batch conditions. Toward its application to continuous-flow synthesis, we considered the description of the reaction mixture as well as the reaction rate
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Published 31 May 2023
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