Elsevier eBooks, Год журнала: 2024, Номер unknown
Опубликована: Янв. 1, 2024
Язык: Английский
Chemical Communications, Год журнала: 2023, Номер 59(90), С. 13450 - 13453
Опубликована: Янв. 1, 2023
Herein, we describe nickel-catalyzed nitrile hydroboration with pinacolborane, wherein a tethered NHC-pyridonate ligand enables efficient catalysis (5 mol% [Ni], ≤6 h reaction time) at room temperature. Mechanistic studies, including isolation of the catalytically relevant intermediates, shed light on cooperative role in activating both reagents simultaneously.
Язык: Английский
Процитировано
10
Beilstein Journal of Organic Chemistry, Год журнала: 2023, Номер 19, С. 325 - 348
Опубликована: Март 21, 2023
Catalysis is dominated by the use of rare and potentially toxic transition metals. The main group offers a sustainable alternative for catalysis, due to generally higher abundance lower toxicity these elements. Group 13 elements have rich catalogue stoichiometric addition reactions unsaturated bonds but cannot undergo redox chemistry which underpins transition-metal catalysis. exchange transfer one or more groups from element another, through σ-bond metathesis; where boron both elements, this termed transborylation. These redox-neutral processes are increasingly being used render traditionally 13-mediated catalytic develop new processes, examples focus review.
Язык: Английский
Процитировано
9
Organic Letters, Год журнала: 2023, Номер 25(43), С. 7923 - 7927
Опубликована: Окт. 26, 2023
We report here the hydroboration of nitriles, alkynes, and carboxylic acids using amidophosphine boranes {(BH3)(PPh2)-NC(CH3)3}, {(BH3)2(PPh)2N(CH2)C6H5}, {(BH3)2(PPh2)2N-(BH3)CH2C6H4N} as reducing agents. These compounds were synthesized to replace more commonly used borane reagents. Solid boranes, which with ease, demonstrated excellent reactivity functional group tolerance toward a wide variety acids, affording corresponding ammonium salts, alkenes, alcohols in good yield.
Язык: Английский
Процитировано
5
Chemical Communications, Год журнала: 2024, Номер 60(77), С. 10748 - 10751
Опубликована: Янв. 1, 2024
Indolines are common motifs within pharamceuticals and natural products. Boron catalysis enables the chemoselective allylation of indoles to give allylic indolines in excellent diastereoselectivity. Mechanistic studies revealed
Язык: Английский
Процитировано
1
New Journal of Chemistry, Год журнала: 2023, Номер 47(24), С. 11544 - 11556
Опубликована: Янв. 1, 2023
We performed a detailed experimental and theoretical analysis of the 1,3-hydride shift in imine–BH 3 adducts, which represents crucial step formation mono-aminoboranes (R 2 N–BH ).
Язык: Английский
Процитировано
3
Synthesis, Год журнала: 2022, Номер 55(01), С. 62 - 74
Опубликована: Окт. 10, 2022
Abstract This review highlights transborylation (controlled boron-boron exchange) and its applications as a turnover strategy in boron-catalysed methodologies. Catalytic of B–C, B–O, B–N, B–F, B–S, B–Se transborylations are discussed the context transborylation-enabled catalysis, across wide range organic transformations including hydroboration, C–C bond formation, C–H borylation, chemoselective reduction, asymmetric reduction. 1 Introduction 2 B–C Transborylation 3 B–O 4 B–N 5 B–F 6 B–S 7 Conclusion
Язык: Английский
Процитировано
5
Organic Letters, Год журнала: 2023, Номер 25(50), С. 8981 - 8986
Опубликована: Дек. 11, 2023
The recent revelation of hidden-borane catalysis has revolutionized the field catalytic hydroboration in organic synthesis. Many nucleophilic reaction promoters, previously believed to be catalysts, fact primarily facilitated formation borane (BH3), which subsequently acted as true catalyst. This prompted us explore untapped potential these unexpected transformations, with a view simplify using more cost-effective and environmentally friendly precatalysts. Via computational studies, we were able identify that water can actually undertake role. Herein, report study on simple nitriles, notoriously challenging yet synthetically valuable class substrates, nothing than moisture an activating agent. moisture-assisted nitrile process seamlessly integrate range downstream transformations one-pot fashion produce N-containing products such symmetrical imines, thioureas, bis(alcohol)amines well N-heterocycles pyrroles, pyridines, pyridinium salts, 2-iminothiazolines, carbazoles.
Язык: Английский
Процитировано
2
Angewandte Chemie, Год журнала: 2024, Номер 136(23)
Опубликована: Апрель 5, 2024
Abstract Silyl‐heterocycles offer a unique handle to expand and explore chemical space, reactivity, functionality. The shortage of catalytic methods for the preparation diverse functionalized silyl‐heterocycles however limits widespread exploration exploitation. Herein borane‐catalyzed intramolecular 1,1‐carboboration silyl‐alkynes has been developed synthesis 2,3‐dihydrosilolyl silylcyclobut‐2‐enyl boronic esters. Successful, carboboration achieved on variety functionally silyl‐alkynes, using borane catalyst transborylation‐enabled turnover. Mechanistic studies, including 13 C‐labelling, computational single‐turnover experiments, suggest reaction pathway proceeding by 1,2‐hydroboration, 1,1‐carboboration, transborylation release alkenyl ester product regenerate catalyst.
Язык: Английский
Процитировано
0
Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(23)
Опубликована: Апрель 5, 2024
Silyl-heterocycles offer a unique handle to expand and explore chemical space, reactivity, functionality. The shortage of catalytic methods for the preparation diverse functionalized silyl-heterocycles however limits widespread exploration exploitation. Herein borane-catalyzed intramolecular 1,1-carboboration silyl-alkynes has been developed synthesis 2,3-dihydrosilolyl silylcyclobut-2-enyl boronic esters. Successful, carboboration achieved on variety functionally silyl-alkynes, using borane catalyst transborylation-enabled turnover. Mechanistic studies, including
Язык: Английский
Процитировано
0
Elsevier eBooks, Год журнала: 2024, Номер unknown
Опубликована: Янв. 1, 2024
Язык: Английский
Процитировано
0