Linear bis‐Coordinate Silver(I) and Iodine(I) Complexes with R3R2R1N Tertiary Amines DOI Creative Commons
Parveen Kumar,

Joonas Komulainen,

Antonio Frontera

et al.

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 29(69)

Published: Sept. 8, 2023

Homoleptic [L-I-L]+ iodine(I) complexes (where L is a R3 R2 R1 N tertiary amine) were synthesized via the [L-Ag-L]+ → cation exchange reaction. In solution, amines form [R3 N-Ag-NR1 ]+ silver(I) complexes, which crystallize out from solution as meso-[L-Ag-L]+ characterized by X-ray crystallography. The subsequent analogues extremely reactive and could not be isolated in solid state. Density functional theory (DFT) calculations performed to study Ag+ -N I+ interaction energies with former ranging -80 -100 kJ mol-1 latter -260 -279 . crystal structures revealed ⋅⋅⋅Cπ ⋅⋅⋅H-C short contacts between flexible N-alkyl/N-aryl groups, are first of their kind such precursor complexes.

Language: Английский

C–H Bond Functionalization of Amines: A Graphical Overview of Diverse Methods DOI Creative Commons

Subhradeep Dutta,

Bowen Li,

Dillon R. L. Rickertsen

et al.

SynOpen, Journal Year: 2021, Volume and Issue: 05(03), P. 173 - 228

Published: July 1, 2021

This Graphical Review provides a concise overview of the manifold and mechanistically diverse methods that enable functionalization sp

Language: Английский

Citations

65
Rhodium hydride enabled enantioselective intermolecular C–H silylation to access acyclic stereogenic Si–H DOI Creative Commons
Kun An,

Wenpeng Ma,

Lichuan Liu

et al.

Nature Communications, Journal Year: 2022, Volume and Issue: 13(1)

Published: Feb. 14, 2022

The tremendous success of stereogenic carbon compounds has never ceased to inspire researchers explore the potentials silicon compounds. Intermolecular C-H silylation thus represents most versatile and straightforward strategy construct C-Si bonds, however, its enantioselective variant been scarcely reported date. Herein we report a protocol that allows for intermolecular bond silylation, leading construction wide array acyclic Si-H under simple mild reaction conditions. Key is (1) substrate design prevents self-reaction prochiral silane (2) employment more reactive rhodium hydride ([Rh]-H) catalyst as opposed commonly used chloride ([Rh]-Cl) catalyst. This work unveils opportunities in converting arenes into value-added

Language: Английский

Citations

59
B(C6F5)3-Catalyzed Dehydrogenation of Pyrrolidines to Form Pyrroles DOI Creative Commons

Ana Alvarez-Montoya,

Joseph P. Gillions,

Laura Winfrey

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(7), P. 4856 - 4864

Published: March 18, 2024

Pyrroles are important N-heterocycles found in medicines and materials. The formation of pyrroles from widely accessible pyrrolidines is a potentially attractive strategy but an underdeveloped approach due to the sensitivity oxidative conditions required achieve such transformation. Herein, we report catalytic that employs commercially available B(C6F5)3 operationally simple procedure allows serve as direct synthons for pyrroles. Mechanistic studies have revealed insights into borane-catalyzed dehydrogenative processes.

Language: Английский

Citations

11
The role of silicon in drug discovery: a review DOI Creative Commons
Jenny‐Lee Panayides, Darren L. Riley, Felix Hasenmaile

et al.

RSC Medicinal Chemistry, Journal Year: 2024, Volume and Issue: 15(10), P. 3286 - 3344

Published: Jan. 1, 2024

This review aims to highlight the role of silicon in drug discovery.

Language: Английский

Citations

10
Consecutive β,β′‐Selective C(sp3)−H Silylation of Tertiary Amines with Dihydrosilanes Catalyzed by B(C6F5)3 DOI Creative Commons
Huaquan Fang, Kaixue Xie, Sebastian Kemper

et al.

Angewandte Chemie International Edition, Journal Year: 2021, Volume and Issue: 60(15), P. 8542 - 8546

Published: Feb. 19, 2021

Tris(pentafluorophenyl)borane has been found to catalyze the two-fold C(sp

Language: Английский

Citations

44
3-Silaazetidine: An Unexplored yet Versatile Organosilane Species for Ring Expansion toward Silaazacycles DOI

Wanshu Wang,

Song Zhou,

Linjie Li

et al.

Journal of the American Chemical Society, Journal Year: 2021, Volume and Issue: 143(29), P. 11141 - 11151

Published: July 19, 2021

Small-ring silacycles are important organosilane species in main-group chemistry and have found numerous applications organic synthesis. 3-Silaazetidine, a unique small silacycle bearing silicon nitrogen atoms, has not been adequately explored due to the lack of general synthetic scheme its sensitivity air. Here, we describe that 3-silaazetidine can be easily prepared situ from diverse air-stable precursors (RSO2NHCH2SiR12CH2Cl). 3-Silaazetidine shows excellent functional group tolerance palladium-catalyzed ring expansion reaction with terminal alkynes, giving 3-silatetrahydropyridines silaazacycle derivatives, which promising frameworks for discovery Si-containing molecules.

Language: Английский

Citations

40
Asymmetric total synthesis and antidepressant activity of (−)-sila-mesembranol bearing a silicon stereocenter DOI
Gan Luo, Lingmin Chen, Yi Li

et al.

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(21), P. 5941 - 5947

Published: Jan. 1, 2021

Asymmetric total synthesis of (−)-sila-mesembranol, the silicon analog natural alkaloid (−)-mesembranol has been achieved in 3.3% yield over 11 steps. The synthetic (−)-sila-mesembranol mice exhibits better antidepressant effects than its carbon counterpart.

Language: Английский

Citations

39
Activation of Si–H and B–H bonds by Lewis acidic transition metals and p-block elements: same, but different DOI Creative Commons
Pablo Ríos, Amor Rodríguez, Salvador Conejero

et al.

Chemical Science, Journal Year: 2022, Volume and Issue: 13(25), P. 7392 - 7418

Published: Jan. 1, 2022

In this

Language: Английский

Citations

26
General Concepts and Recent Advances in the Electrochemical Transformation of Chloro‐ and Hydrosilanes DOI Creative Commons
Alexander D. Beck, Stefan Haufe, Siegfried R. Waldvogel

et al.

ChemElectroChem, Journal Year: 2023, Volume and Issue: 10(4)

Published: Jan. 23, 2023

Abstract Organosilanes play an important role in organic synthesis as well a variety of further areas, ranging from life science to transportation. Especially, the electrochemical access has become increasingly past years and developed into essential topic due new conceptual approaches mediated reaction control. With commercial availability high‐quality equipment, technical requirements for electro‐conversion are at hand wide audience. This results need concise survey silane transformation, appropriate novices experts alike. review provides overview most relevant work this field, identifies common obstacles working with chlorosilanes hydrosilanes bridges gap between known techniques novel methods respect their conversion. The historical development is outlined reference various cathodic anodic conversions should encourage expand research field transformation.

Language: Английский

Citations

14
B(C6F5)3-catalyzed β-C(sp3)–H alkylation of tertiary amines with 2-aryl-3H-indol-3-ones DOI

Changpeng Zou,

Tao Ma,

Xiu‐Xiu Qiao

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(21), P. 4393 - 4397

Published: Jan. 1, 2023

Herein, we describe a B(C 6 F 5 ) 3 -catalyzed redox-neutral β-functionalization of tertiary amines with cyclic-ketimines, achieving various 1,3-diamines containing the indolin-3-one moiety via borrowing hydrogen strategy.

Language: Английский

Citations

14