Recent Advances in Hydrometallation of Alkenes and Alkynes via the First Row Transition Metal Catalysis

Chinese Journal of Chemistry, Journal Year: 2018, Volume and Issue: 36(11), P. 1075 - 1109

Published: Aug. 20, 2018

Abstract Hydrometallation of alkenes and alkynes provides a straightforward route to access alkyl‐ or alkenyl‐metal reagents, which have wide range applications in organic transformations. In recent years, the first row transition metals (such as copper, nickel, cobalt, iron, etc .) emerged high activity selectivity this area with aid variety ligands. This review covers advances hydrometallation minimally functionalized unsaturated C—C bonds (including alkenes, alkynes, dienes, allenes, enynes, .), well transformations involving catalytic process via metal catalysis.

Language: Английский

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Hydride Transfer Reactions Catalyzed by Cobalt Complexes

Chemical Reviews, Journal Year: 2018, Volume and Issue: 119(4), P. 2876 - 2953

Published: Dec. 19, 2018

Cobalt has become increasingly attractive in homogeneous catalysis because of its unique characteristics and outstanding catalytic performance addition to being cheap earth-abundant. Hydride transfer processes are involved a broad range organic transformations that allow the facile preparation various useful chemicals synthetic building blocks. These reactions have continuously received great attention both from academia industry. In this perspective, we review cobalt-catalyzed hydride according classified reaction types provide comprehensive overview design, synthesis, reactivity cobalt catalysts, their applications, mechanisms.

Language: Английский

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First-Row d-Block Element-Catalyzed Carbon–Boron Bond Formation and Related Processes

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

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Recent advances in tridentate iron and cobalt complexes for alkene and alkyne hydrofunctionalizations

Coordination Chemistry Reviews, Journal Year: 2019, Volume and Issue: 386, P. 138 - 153

Published: Feb. 18, 2019

Language: Английский

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Cobalt-Catalyzed (E)-Selective anti-Markovnikov Hydrosilylation of Terminal Alkynes

ACS Catalysis, Journal Year: 2018, Volume and Issue: 8(7), P. 5896 - 5900

Published: May 23, 2018

We report a regioselective and stereoselective hydrosilylation of terminal alkynes with catalysts generated from bench-stable Co(acac)2 bisphoshpine ligands. The cobalt catalyst precursors are activated by the reaction hydrosilanes, air-sensitive activators, such as Grignard reagents or NaBHEt3, not required for activation. A wide range aromatic aliphatic underwent this cobalt-catalyzed hydrosilylation, affording corresponding (E)-vinylsilanes in high yields regioselectivity stereoselectivity. These reactions show good functional group compatibility can be readily scaled up to gram-scales without using drybox. Deuterium-labeling experiments suggest cis-addition hydrosilanes alkynes.

Language: Английский

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Direct Synthesis of Multi(boronate) Esters from Alkenes and Alkynes via Hydroboration and Boration Reactions

ACS Catalysis, Journal Year: 2020, Volume and Issue: 11(1), P. 1 - 18

Published: Dec. 10, 2020

Multi(boronate) esters have been attracting increasing attention as versatile building blocks for the succinct and precise synthesis of complex molecules. However, there are a limited number efficient synthetic procedures available. In this respect, direct multiboration alkenes alkynes is undoubtedly an ideal route their synthesis. During past 30 years, catalytic systems based on transition-metals, organophosphines, bases, even catalyst-free systems, with heat or light irradiation straightforward preparation from developed. different numbers (up to 4) positional relationships adjacent boron moieties were obtained, which summarized discussed herein.

Language: Английский

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Versatile Cobalt-Catalyzed Enantioselective Entry to Boryl-Functionalized All-Carbon Quaternary Stereogenic Centers

Journal of the American Chemical Society, Journal Year: 2018, Volume and Issue: 140(34), P. 10687 - 10690

Published: Aug. 16, 2018

We report an asymmetric synthesis of chiral boryl-functionalized γ-lactams containing all-carbon quaternary stereocenters via a Co-catalyzed enantioselective hydroboration/cyclization amide-tethered 1,6-enynes. These enantio-enriched γ-lactam products can be readily converted to variety cyclic and acyclic other γ-lactams, pyrrolidin-2,3-diones, β-amino acid N-carboxyanhydrides, carboxylic amides.

Language: Английский

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Generation and Application of (Diborylmethyl)zinc(II) Species: Access to Enantioenriched gem‐Diborylalkanes by an Asymmetric Allylic Substitution

Angewandte Chemie International Edition, Journal Year: 2018, Volume and Issue: 57(39), P. 12930 - 12934

Published: July 2, 2018

We report the successful generation of (diborylmethyl)zinc(II) species by transmetallation beteween isolable (diborylmethyl)lithium and zinc(II) halide (X=Br, Cl) their application in synthesis enantioenriched gem-diborylalkanes bearing a stereogenic center at β-position diboryl groups an asymmetric allylic substitution reaction. The reaction has broad substrate scope, various can be obtained good yields with excellent enantioselectivity. Further elaboration provides access to diverse set valuable chiral building blocks.

Language: Английский

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Copper-catalyzed asymmetric hydroboration of 1,3-enynes with pinacolborane to access chiral allenylboronates

Organic Chemistry Frontiers, Journal Year: 2018, Volume and Issue: 5(8), P. 1284 - 1287

Published: Jan. 1, 2018

A wide range of functionalized 1,3-enynes undergo hydroboration with pinacolborane to produce enantiomerically enriched allenylboronates in the presence a chiral copper catalyst.

Language: Английский

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Versatile cobalt-catalyzed regioselective chain-walking double hydroboration of 1,n-dienes to access gem-bis(boryl)alkanes

Nature Communications, Journal Year: 2020, Volume and Issue: 11(1)

Published: Feb. 7, 2020

Abstract Double hydroboration of dienes is the addition a hydrogen and boryl group to two double bonds diene molecule represents straightforward effective protocol prepare synthetically versatile bis(boryl)alkanes, provided that this reaction occurs selectively. However, can potentially yield several isomeric organoboron products, it still remains challenge control regioselectivity reaction, which allows selective production single product, in particular, for broad scope dienes. By employing readily available cobalt catalyst, here we show yields useful gem -bis(boryl)alkanes with excellent regioselectivity. In addition, encompasses wide range conjugated non-conjugated Furthermore, mechanistic studies indicate cobalt-catalyzed through boryl-directed chain-walking alkenylboronates generated from anti -Markovnikov 1,2-hydroboration 1,n-diene.

Language: Английский

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