The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(11), С. 7162 - 7171
Опубликована: Май 10, 2023
Herein, we have demonstrated a simple nickel-catalyzed C-3-selective alkylation of 2-oxindoles using wide variety secondary alkyl alcohols. As special highlight, functionalization the cholesterol derivative was reported. Control experiments, initial mechanistic studies, and deuterium-labeling experiments were performed for process.
Язык: Английский
ACS Central Science, Год журнала: 2021, Номер 7(4), С. 570 - 585
Опубликована: Март 25, 2021
Borrowing hydrogen is a process that used to diversify the synthetic utility of commodity alcohols. A catalyst first oxidizes an alcohol by removing form reactive carbonyl compound. This intermediate can undergo diverse range subsequent transformations before returns "borrowed" liberate product and regenerate catalyst. In this way, alcohols may be as alkylating agents whereby sole byproduct one-pot reaction water. recent decades, significant advances have been made in area, demonstrating many effective methods access valuable products. outlook highlights diversity metal biocatalysts are available for approach, well various performed, focusing on selection most advances. By succinctly describing conveying versatility borrowing chemistry, we anticipate its uptake will increase across wider scientific audience, expanding opportunities further development.
Язык: Английский
Процитировано
318
ACS Catalysis, Год журнала: 2019, Номер 9(9), С. 8575 - 8580
Опубликована: Авг. 21, 2019
Herein we report the iron-catalyzed β-C(sp3)-methylation of primary alcohols using methanol as a C1 building block. This borrowing hydrogen approach employs well-defined bench-stable (cyclopentadienone)iron(0) carbonyl complex precatalyst (5 mol %) and enables diverse selection substituted 2-arylethanols to undergo in good isolated yields (24 examples, 65% average yield).
Язык: Английский
Процитировано
93
Organic Letters, Год журнала: 2020, Номер 22(5), С. 2064 - 2069
Опубликована: Фев. 24, 2020
An iron-catalyzed borrowing hydrogen strategy has been applied in the synthesis of β-branched carbonyl compounds. Various secondary benzylic and aliphatic alcohols have used as alkylating reagents under mild reaction conditions. The ketones isolated good to excellent yield. Deuterium labeling experiments provide evidence that alcohol is hydride source this no reversible step or hydrogen/deuterium scrambling takes place during process.
Язык: Английский
Процитировано
75
Green Chemistry, Год журнала: 2022, Номер 24(6), С. 2602 - 2612
Опубликована: Янв. 1, 2022
Porous polypyridine-oxadiazole supported iridium catalysts (PPO-Ir) revealed high catalytic activity for the reaction of dimethyl-6-aminouracil (including 1,3-dimethylbarbituric acid, 2-aminobenzylamine) with alcohols.
Язык: Английский
Процитировано
53
ChemSusChem, Год журнала: 2019, Номер 12(11), С. 2345 - 2349
Опубликована: Апрель 8, 2019
A general and efficient iron-catalyzed C-alkylation of oxindoles has been developed. This borrowing hydrogen approach employing a (cyclopentadienone)iron carbonyl complex (2 mol %) exhibited broad reaction scope, allowing benzylic simple primary secondary aliphatic alcohols to be employed as alkylating agents. variety underwent selective mono-C3-alkylation in good-to-excellent isolated yields (28 examples, 50-92 % yield, 79 average yield).
Язык: Английский
Процитировано
65
Chemical Communications, Год журнала: 2020, Номер 56(98), С. 15442 - 15445
Опубликована: Янв. 1, 2020
A nickel catalysed chemoselective C3-alkylation of indole is reported that follows a borrowing hydrogen method promoted by radical.
Язык: Английский
Процитировано
65
Organic Letters, Год журнала: 2019, Номер 21(20), С. 8404 - 8408
Опубликована: Окт. 7, 2019
β-Branched alkylated alcohols have been prepared in good yields using a double-hydrogen autotransfer strategy the presence of our diaminocyclopentadienone iron tricarbonyl complex Fe1. The alkylation some 2-arylethanol derivatives was successfully addressed with benzylic and methanol as alkylating reagents under mild conditions. Deuterium labeling experiments suggested that both (2-arylethanol either or benzyl alcohol) served hydrogen donors this cascade process.
Язык: Английский
Процитировано
58
ChemSusChem, Год журнала: 2020, Номер 13(10), С. 2557 - 2563
Опубликована: Март 31, 2020
Abstract A sustainable and green route to access diverse functionalized ketones via dehydrogenative–dehydrative cross‐coupling of primary secondary alcohols is demonstrated. This borrowing hydrogen approach employing a pincer N‐heterocyclic carbene Mn complex displays high activity selectivity. variety are well tolerant result in satisfactory isolated yields. Mechanistic studies suggest that this reaction proceeds direct outer‐sphere mechanism the dehydrogenation alcohol substrates plays vital role rate‐limiting step.
Язык: Английский
Процитировано
58
ACS Catalysis, Год журнала: 2020, Номер 10(14), С. 8023 - 8031
Опубликована: Июнь 26, 2020
Oxindoles have been successfully α-alkylated under Cp*CoIII catalysis by a vast array of secondary alcohols, including cyclic, acyclic, symmetrical, and unsymmetrical, to produce C-alkylated oxindoles. This protocol was also extended the α-alkylation N,N-dimethyl barbituric acid benzyl cyanides. The kinetic profile other preliminary mechanistic investigations suggest first-order reaction rate in oxindoles catalysts. A plausible catalytic cycle is proposed on basis profile, investigations, previous studies similar transformations, whereas density functional theory calculations provide insight into nature active species.
Язык: Английский
Процитировано
55
The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(6), С. 3989 - 4000
Опубликована: Март 8, 2022
Herein, we demonstrated Mn-catalyzed selective C-3 functionalization of indoles with alcohols. The developed catalyst can also furnish bis(indolyl)methanes from the same set substrates under slightly modified reaction conditions. Mechanistic studies reveal that is going via a borrowing hydrogen pathway. To highlight practical utility, diverse range including nine structurally important drug molecules are synthesized. Furthermore, introduced one-pot cascade strategy for synthesizing functionalized directly 2-aminophenyl ethanol and alcohol.
Язык: Английский
Процитировано
36