Aluminum Amidinates: Insights into Alkyne Hydroboration DOI Creative Commons
Katie Hobson, Claire J. Carmalt, Clare Bakewell

et al.

Inorganic Chemistry, Journal Year: 2021, Volume and Issue: 60(15), P. 10958 - 10969

Published: July 16, 2021

The mechanism of the aluminum-mediated hydroboration terminal alkynes was investigated using a series novel aluminum amidinate hydride and alkyl complexes bearing symmetric asymmetric ligands. new were fully characterized found to facilitate formation (E)-vinylboronate product, with rates orders reaction linked complex size stability. Kinetic analysis stoichiometric reactions used elucidate mechanism, which we propose proceed via initial an Al-borane adduct. Additionally, most unstable promote decomposition pinacolborane substrate borane (BH3), can then catalyze reaction. This is in contrast previously reported hydride-catalyzed reactions, are proposed acetylide, or by hydroalumination form vinylboronate ester as first step catalytic cycle.

Language: Английский

First-Row d-Block Element-Catalyzed Carbon–Boron Bond Formation and Related Processes DOI
Shubhankar Kumar Bose, Lujia Mao,

Laura Kuehn

et al.

Chemical Reviews, Journal Year: 2021, Volume and Issue: 121(21), P. 13238 - 13341

Published: Oct. 7, 2021

Organoboron reagents represent a unique class of compounds because their utility in modern synthetic organic chemistry, often affording unprecedented reactivity. The transformation the carbon–boron bond into carbon–X (X = C, N, and O) stereocontrolled fashion has become invaluable medicinal agrochemistry, natural products chemistry as well materials science. Over past decade, first-row d-block transition metals have increasingly widely used catalysts for formation bond, traditionally catalyzed by expensive precious metals. This recent focus on alternative enabled growth fundamental methods organoboron chemistry. review surveys current state-of-the-art use element-based bonds.

Language: Английский

Citations

238

The transition metal-catalysed hydroboration reaction DOI Creative Commons
Stephen J. Geier, Christopher M. Vogels, Jennifer A. Melanson

et al.

Chemical Society Reviews, Journal Year: 2022, Volume and Issue: 51(21), P. 8877 - 8922

Published: Jan. 1, 2022

This review covers the development of transition metal-catalysed hydroboration reaction, from its beginnings in 1980s to more recent developments including earth-abundant catalysts and an ever-expanding array substrates.

Language: Английский

Citations

144

s-Block Metal Catalysts for the Hydroboration of Unsaturated Bonds DOI Creative Commons
Marc Magre, Marcin Szewczyk, Magnus Rueping

et al.

Chemical Reviews, Journal Year: 2022, Volume and Issue: 122(9), P. 8261 - 8312

Published: March 7, 2022

The addition of a B–H bond to an unsaturated (polarized or unpolarized) is powerful and atom-economic tool for the synthesis organoboranes. In recent years, s-block organometallics have appeared as alternative catalysts transition-metal complexes, which traditionally catalyze hydroboration bonds. Because rapid development in field bonds catalyzed by alkali (Li, Na, K) alkaline earth (Mg, Ca, Sr, Ba) metals, we provide detailed updated comprehensive review that covers synthesis, reactivity, application metal polarized well carbon–carbon Moreover, describe main reaction mechanisms, providing valuable insight into reactivity catalysts. Finally, compare these complexes with other redox-neutral catalytic systems based on p-block metals including aluminum f-block lanthanides early actinides. this review, aim comprehensive, authoritative, critical assessment state art within highly interesting research area.

Language: Английский

Citations

112

Overview of Regioselective and Stereoselective Catalytic Hydroboration of Alkynes DOI
Supriya Rej, Amrita Das, Tarun K. Panda

et al.

Advanced Synthesis & Catalysis, Journal Year: 2021, Volume and Issue: 363(21), P. 4818 - 4840

Published: Sept. 16, 2021

Abstract Hydroboration of alkynes is special interest to researchers since it the most straightforward process for synthesis highly important vinylborane synthetic intermediate compounds. It significant in terms both regioselectivity and stereoselectivity, several positional isomers are formed during hydroboration. Given importance this class compounds, an extensive study has been carried out regarding catalytic condition development detailed mechanistic studies selectively obtaining a single isomer. This review comprehensively summarizes regioselective stereoselective hydroboration alkynes. aimed at giving readers accurate knowledge systems available certain We anticipate that inclusive will encourage explore more new types achieve remarkable magnified image

Language: Английский

Citations

94

Low-Valent Tungsten Catalysis Enables Site-Selective Isomerization–Hydroboration of Unactivated Alkenes DOI
Tanner C. Jankins,

Raúl Martín‐Montero,

Phillippa Cooper

et al.

Journal of the American Chemical Society, Journal Year: 2021, Volume and Issue: 143(37), P. 14981 - 14986

Published: Sept. 9, 2021

A tungsten-catalyzed hydroboration of unactivated alkenes at distal C(sp

Language: Английский

Citations

58

Hydroelementation of diynes DOI Creative Commons
Jędrzej Walkowiak, Jakub Szyling, Adrian Franczyk

et al.

Chemical Society Reviews, Journal Year: 2022, Volume and Issue: 51(3), P. 869 - 994

Published: Jan. 1, 2022

This review highlights the hydroelementation reactions of conjugated and separated diynes, which depending on process conditions, catalytic system, as well type reagents, leads to formation various products: enynes, dienes, allenes, polymers, or cyclic compounds. The presence two triple bonds in diyne structure makes these compounds important reagents but selective product is often difficult owing problems associated with maintaining appropriate reaction regio- stereoselectivity. Herein we this topic gain knowledge reactivity diynes systematise range information relating their use reactions. divided according addition E-H (E = Mg, B, Al, Si, Ge, Sn, N, P, O, S, Se, Te) bond bond(s) diyne, reagent used, formed. Not only are comprehensively discussed, synthetic potential obtained products also presented. majority published research included within review, illustrating limitations processes, intent showcase power transformations synthesis materials chemistry.

Language: Английский

Citations

47

Triethoxysilane-Catalyzed Single and Sequential Regioselective Hydroboration of Terminal Alkynes: Sustainable Access to E-Alkenylboronate and Alkyl Gem-Diboronate Esters by Non-Covalent Interactions DOI

Harleen Kaur,

Himani Ahuja,

Rebeca Arévalo

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 976 - 981

Published: Jan. 1, 2025

Triethoxysilane was found to be an efficient catalyst for the synthesis of E-alkenyl- and alkyl-di-boronate esters by single sequential hydroboration terminal alkynes, respectively, with pinacolborane. Mechanistic studies support that formation diboronate proceeds a double pathway steric electronic profile at Si being key enabling second step. Weak non-covalent interactions involving C≡C or C═C bonds in alkynes alkenylboronate have been identified as responsible substrate activation toward addition HBPin.

Language: Английский

Citations

1

Alkylzinc complexes derived from formylfluorenimide ligands: Synthesis, characterization and catalysis for hydroboration of aldehydes and ketones DOI
Biao Wei,

Zhibiao Qin,

Hui Miao

et al.

Dalton Transactions, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Five new alkyl zinc complexes supported by different formylfluorenimide ligands were prepared and characterized.

Language: Английский

Citations

1

Manganese‐Catalyzed Hydroborations with Broad Scope DOI Creative Commons
Pradip Ghosh, Axel Jacobi von Wangelin

Angewandte Chemie International Edition, Journal Year: 2021, Volume and Issue: 60(29), P. 16035 - 16043

Published: April 24, 2021

Reductive transformations of easily available oxidized matter are at the heart synthetic manipulation and chemical valorization. The applications catalytic hydrofunctionalization benefit from use liquid reducing agents operationally facile setups. Metal-catalyzed hydroborations provide a highly prolific platform for reductive valorizations stable C=X electrophiles. Here, we report an especially facile, broad-scope reduction various functions including carbonyls, carboxylates, pyridines, carbodiimides, carbonates under very mild conditions with inexpensive pre-catalyst Mn(hmds)2 . reaction could be successfully applied to depolymerizations.

Language: Английский

Citations

54

Aluminium complexes: next-generation catalysts for selective hydroboration DOI
Amrita Das, Supriya Rej, Tarun K. Panda

et al.

Dalton Transactions, Journal Year: 2022, Volume and Issue: 51(8), P. 3027 - 3040

Published: Jan. 1, 2022

Development of efficient Al-complexes and their crucial roles in catalytic selective hydroboration several unsaturated compounds such as carbonyls, alkenes, alkynes, imines, nitriles others were well documented this review.

Language: Английский

Citations

35