Organic Chemistry Frontiers, Год журнала: 2022, Номер 9(13), С. 3428 - 3437
Опубликована: Янв. 1, 2022
A novel dehydrogenative C–C bond formation of indoles and N -tosylhydrazones to give di(indolyl)methanes (DIMs) has been demonstrated using tris(pentafluorophenyl)borane as a catalyst.
Язык: Английский
Angewandte Chemie International Edition, Год журнала: 2019, Номер 58(11), С. 3579 - 3583
Опубликована: Янв. 9, 2019
Abstract A straightforward gram‐scale preparation of cyclohexa‐1,4‐diene‐based hydrogen cyanide (HCN) surrogates is reported. These are bench‐stable but formally release HCN and rearomatize when treated with Lewis acids. For BCl 3 , the formation isocyanide adduct [(CN)BCl ] − corresponding Wheland complex was verified by mass spectrometry. In presence 1,1‐di‐ trisubstituted alkenes, transfer from surrogate to C−C double bond occurs, affording highly substituted nitriles Markovnikov selectivity. The success this hydrocyanation depends on acid employed; catalytic amounts (C 6 F 5 ) 2 shown be effective while B(C BF ⋅OEt not.
Язык: Английский
Процитировано
34
Green Chemistry, Год журнала: 2023, Номер 25(2), С. 746 - 754
Опубликована: Янв. 1, 2023
Described herein is an unconventional catalyst-free transfer hydrogenation reaction of activated alkenes using isopropanol as eco-friendly reductant and solvent.
Язык: Английский
Процитировано
10
Organic & Biomolecular Chemistry, Год журнала: 2018, Номер 16(9), С. 1448 - 1451
Опубликована: Янв. 1, 2018
Transfer hydrogenations of imines with Hantzsch esters were realized using 0.1 mol% B(C6F5)3, and up to 38% ee was obtained for asymmetric reactions.
Язык: Английский
Процитировано
26
Synlett, Год журнала: 2019, Номер 30(20), С. 2216 - 2232
Опубликована: Ноя. 6, 2019
A current research program in our laboratory is devoted to the development of cyclohexa-1,4-diene-based surrogates difficult-to-handle compounds and their application metal-free ionic transfer reactions. These investigations grew from interest silylium ion chemistry consequently concentrated initially on gaseous explosive hydrosilanes such as Me3SiH even monosilane (SiH4). Since then, we have expanded concept design other species including H2, mineral acids (HI HBr), hydrocarbons (isobutane isobutene). This Account summarizes discoveries this area date, describing challenges faced along way how combatted them. 1 Introduction 2 Transfer Hydrofunctionalization: Variation Electrofuge 3 Nucleofuge 4 Hydrohalogenation Using a Modified Surrogate 5 Synthesis 6 Conclusion
Язык: Английский
Процитировано
24
Organic Letters, Год журнала: 2020, Номер 22(4), С. 1628 - 1632
Опубликована: Фев. 11, 2020
The regioselective and regiodivergent addition of H-D to a variety 1,1-diarylalkenes was realized utilizing selectively deuterated dihydroaromatic compounds, which were generated by cobalt catalysis. reaction initiated catalytic amounts BF3·Et2O abstracting hydride or deuteride ions from the respective reducing agents led highly incorporation deuterium hydrogen at desired positions starting material.
Язык: Английский
Процитировано
22
Angewandte Chemie International Edition, Год журнала: 2021, Номер 60(44), С. 23661 - 23666
Опубликована: Сен. 3, 2021
Indium tribromide catalysed the transfer hydrogenation from dihydroaromatic compounds, such as commercially available γ-terpinene, to enones, which resulted in cyclisation trisubstituted furan derivatives. The reaction was initiated by a Michael addition of hydride nucleophile enone subunit followed Lewis-acid-assisted and formation furan-indium intermediate Wheland derived starting material. product formed protonation complex replaced indium substituent. In addition, site-specific deuterium labelling HD surrogates site specific products gave useful insights into mechanism H-D scrambling.
Язык: Английский
Процитировано
19
The Journal of Organic Chemistry, Год журнала: 2019, Номер 84(10), С. 6312 - 6322
Опубликована: Апрель 19, 2019
An effective nickel-catalyzed cross-coupling of Umpolung carbonyls and alkyl halides was developed. Complementary to classical alkylation techniques, this reaction utilizes as the environmentally benign nucleophiles, providing an efficient selective catalytic alternative traditional use highly reactive organometallic reagents.
Язык: Английский
Процитировано
22
Organic Letters, Год журнала: 2019, Номер 21(12), С. 4531 - 4534
Опубликована: Май 31, 2019
A transfer hydrobromination of C-C triple bonds inititated by Brønsted acids is reported. Hydrogen bromide released stepwise from a bench-stable cyclohexa-1,4-diene-based surrogate, generating biphenyl and ethylene as waste. range vinyl bromides was prepared terminal internal, mainly acceptor-substituted alkynes with good functional-group tolerance.
Язык: Английский
Процитировано
21
Angewandte Chemie, Год журнала: 2019, Номер 132(7), С. 2737 - 2741
Опубликована: Дек. 6, 2019
Abstract Molecular compounds featuring nitrogen atoms are typically regarded as Lewis bases and extensively employed donor ligands in coordination chemistry or nucleophiles organic chemistry. By contrast, electrophilic nitrogen‐containing much rarer. Nitrenium cations a new family of nitrogen‐based acids, the reactivity which remains largely unexplored. In this work, nitrenium ions explored catalysts five transformations. These reactions first examples acid catalysis employing site substrate activation. Moreover, these readily accessed from commercially available reagents exhibit remarkable stability toward moisture, allowing for benchtop transformations without need to pretreat solvents.
Язык: Английский
Процитировано
21
Organic Letters, Год журнала: 2019, Номер 21(17), С. 7129 - 7133
Опубликована: Авг. 19, 2019
We report a contra-thermodynamic isomerization of internal olefins to terminal driven by redox reactions and formation Si–F bonds. This process involves chain-walking hydrosilylation subsequent formal retro-hydrosilylation. The rests upon the high activities platinum catalysts for metal alkyl intermediates new, metal-free conversion alkylsilanes alkenes. By this approach, 1,2-disubstituted trisubstituted are converted olefins.
Язык: Английский
Процитировано
20