Chinese Journal of Organic Chemistry, Год журнала: 2023, Номер 43(5), С. 1777 - 1777
Опубликована: Янв. 1, 2023
A convenient approach acess to boronic ester containing N,O-acetal structure has been established through the Fe(OTf)3-catalyzed addition of with organic boric acid.A series N-O-acetal compounds have successfully prepared in 58%～98% yields.Moreover, these retain property and can be used for coupling reaction.
Язык: Английский
Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(23)
Опубликована: Апрель 2, 2024
The diversified synthesis of chiral fluorinated cyclobutane derivatives has remained a difficult task in synthetic chemistry. Herein, we present an approach for asymmetric hydroboration and formal hydrodefluorination gem-difluorinated cyclobutenes through rhodium catalysis, providing α-boryl cyclobutanes monofluorinated with excellent regio- enantioselectivity, respectively. key to the success two transformations relies on efficient, mild highly selective rhodium-catalyzed HBPin (pinacolborane), which subsequent addition base, catalytic amount palladium some cases, results formation products four-membered ring retained. obtained are versatile building blocks that provide platform enantioenriched great diversity.
Язык: Английский
Процитировано
12
ACS Catalysis, Год журнала: 2024, Номер 14(20), С. 15790 - 15798
Опубликована: Окт. 10, 2024
Here, we report a photoredox and nickel-catalyzed cross-electrophile coupling strategy for the asymmetric three-component 1,2-alkylarylation of vinyl boronates with (hetero)aryl bromides (2°, 3°)-alkyl redox-active esters in presence Hantzsch ester. With fluorinated pyridyl-substituted chiral biimidazoline ligand, this reaction enables straightforward access to wide variety synthetically valuable α-aryl from readily available starting materials. This features mild conditions, broad substrate generality, good functional group tolerance proceeds without using metal reductants or alkyl halides. Furthermore, alkenyl halides other electron-deficient alkenes such as acrylates phosphonates can be applied successfully. Preliminary mechanistic studies shed light on potential pathways roles organic amines.
Язык: Английский
Процитировано
7
European Journal of Organic Chemistry, Год журнала: 2023, Номер 26(43)
Опубликована: Сен. 8, 2023
Abstract Palladium‐catalyzed asymmetric hydrofunctionalization of alkenes is one the most powerful and straightforward methods to forge a new C−H bond C−X (X=C, N, O, F, Si etc) bond, which provides an efficient way obtain valuable enantioenriched molecules from cheap readily available feedstocks. Catalytic simple challenging but still highly sought after. This review will mainly focus on recent advances in Palladium catalyzed over past decade, including hydroamination, hydrooxygenation, hydrofluorination, hydrosilylation, hydroarylation, hydroalkenylation hydrocarbonylation.
Язык: Английский
Процитировано
16
ACS Catalysis, Год журнала: 2023, Номер 14(1), С. 418 - 425
Опубликована: Дек. 20, 2023
Miyaura borylation is widely recognized as one of the most reliable methods for constructing an organoboron compound. Reported herein Pd(0)-catalyzed asymmetric three-component Heck–Miyaura with interception internal olefin, aryldiazonium salt, and diboron reagent. This Heck-triggered protocol proceeds in a highly chemoselective, diastereoselective, enantioselective manner, thus allowing expedient construction 1,2-diaryl substituted β-aminoboronate esters derivatives vicinal stereogenic centers. The versatility resulting benzylic boronic allows their further transformation to more-intricate chiral amines.
Язык: Английский
Процитировано
9
Advanced Science, Год журнала: 2023, Номер 10(35)
Опубликована: Окт. 25, 2023
Abstract Catalytic asymmetric hydroboration of fluoroalkyl‐substituted alkenes is a straightforward approach to access chiral small molecules possessing both fluorine and boron atoms. However, enantioselective without elimination has been long‐standing challenge in this field. Herein, copper‐catalyzed difluoroalkyl‐substituted internal with high levels regio‐ enantioselectivities reported. The native carbonyl directing group, copper hydride system, bisphosphine ligand play crucial roles suppressing the undesired fluoride elimination. This atom‐economic protocol provides practical synthetic platform obtain wide scope enantioenriched secondary boronates bearing difluoromethylene moieties under mild conditions. Synthetic applications including functionalization biorelevant molecules, versatile functional group interconversions, preparation difluoroalkylated Terfenadine derivative are also demonstrated.
Язык: Английский
Процитировано
6
ACS Catalysis, Год журнала: 2024, Номер 14(6), С. 3977 - 3985
Опубликована: Фев. 28, 2024
Asymmetric hydroboration is among the most powerful and straightforward methods to construct chiral organoboron compounds, which are extensively used in natural products, bioactive molecules, materials science. Among them, enantioselective of a single functional group has been well-established experienced significant advances, but asymmetric multiple groups rarely developed due extremely challenging chemo-, regio-, enantioselectivity control. Herein, we present Co-catalyzed enantio- regioselective dihydroboration enals achieved both C═O bond C═C bond. This protocol features mild reaction conditions, wide substrate scope, good tolerance provides highly efficient method for preparation valuable 1,4-borylethers their downstream products such as 1,4-diols amino alcohols. Preliminary mechanistic studies suggested that this involved tandem 1,2-hydroboration/dissociative isomerization/asymmetric process.
Язык: Английский
Процитировано
2
Chinese Journal of Organic Chemistry, Год журнала: 2024, Номер 44(11), С. 3273 - 3273
Опубликована: Янв. 1, 2024
Язык: Английский
Процитировано
2
Molecules, Год журнала: 2024, Номер 29(15), С. 3677 - 3677
Опубликована: Авг. 2, 2024
Organic fluorides are widely used in pharmaceuticals, agrochemicals, material sciences, and other fields due to the special physical chemical properties of fluorine atoms. The synthesis alkyl fluorinated compounds bearing multiple contiguous stereogenic centers is most challenging research area synthetic chemistry has received extensive attention from chemists. This review summarized important progress field over past decade, including asymmetric electrophilic fluorination elaboration substrates (such as allylic alkylation reactions, hydrofunctionalization Mannich addition Michael aldol miscellaneous reactions), with an emphasis on methodologies, substrate scopes, reaction mechanisms.
Язык: Английский
Процитировано
1
Chinese Journal of Organic Chemistry, Год журнала: 2023, Номер 43(5), С. 1761 - 1761
Опубликована: Янв. 1, 2023
A cobalt-catalyzed remote hydroboration of enamines via a sequence chain walking and in the presence an earth abundant catalyst commercially available ligand is reported, providing rapid access to borylamines.This protocol exhibites mild reaction conditions, broad substrate scope good functional group compatibility.In addition, practicability potential synthesis value this were demonstrated by gram variety synthetic transformations borylamine products.
Язык: Английский
Процитировано
2
Chinese Journal of Organic Chemistry, Год журнала: 2023, Номер 43(5), С. 1751 - 1751
Опубликована: Янв. 1, 2023
The transition metal-catalyzed hydroboration of alkenes and alkynes is one the most efficient way for production boronate esters.This type reaction 100% atom economic, starting material readily available, products are diverse.It noticed that known catalytic systems based on late-transition-metals such as Rh, Ir, Pd, Pt, Co, Fe Cu.The use early-transition-metals zirconium titanium, other hand, very scarce.In this short review, development application in titanium mediated alkene alkyne summarized, research trends area also discussed.
Язык: Английский
Процитировано
1