Chemoselective Hydroboration of Propargylic Alcohols and Amines Using a Manganese(II) Catalyst DOI

Aleksandra Brzozowska,

Viktoriia Zubar,

Ruth-Christine Ganardi

et al.

Organic Letters, Journal Year: 2020, Volume and Issue: 22(10), P. 3765 - 3769

Published: March 31, 2020

The first manganese-catalyzed hydroboration of propargylic alcohols and amines as well internal alkynes is reported. High regio- stereoselectivity achieved by applying 2 mol % a manganese precatalyst based on the readily accessible bis(imino)pyridine ligand MnCl2 metal source. Propargylic amines, symmetric alkynes, were efficiently converted into corresponding functionalized alkenes, which can serve important valuable intermediates for further synthetic applications such cross-coupling reactions.

Language: Английский

Strategies and mechanisms of metal–ligand cooperativity in first-row transition metal complex catalysts DOI
Matthew R. Elsby, R. Tom Baker

Chemical Society Reviews, Journal Year: 2020, Volume and Issue: 49(24), P. 8933 - 8987

Published: Jan. 1, 2020

The use of metal–ligand cooperation (MLC) by transition metal bifunctional catalysts has emerged at the forefront homogeneous catalysis science.

Language: Английский

Citations

240

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

Recent advances in the catalytic hydroboration of carbonyl compounds DOI
Mahadev L. Shegavi, Shubhankar Kumar Bose

Catalysis Science & Technology, Journal Year: 2019, Volume and Issue: 9(13), P. 3307 - 3336

Published: Jan. 1, 2019

The latest development in the catalytic hydroboration of CO groups is summarized this review. Access to borate ester intermediates provides a pathway convert them into corresponding valuable functionalized alcohols.

Language: Английский

Citations

171

Manganese-catalyzed hydrogenation, dehydrogenation, and hydroelementation reactions DOI
Kuhali Das, Satyadeep Waiba, Akash Jana

et al.

Chemical Society Reviews, Journal Year: 2022, Volume and Issue: 51(11), P. 4386 - 4464

Published: Jan. 1, 2022

The emerging field of organometallic catalysis has shifted towards research on Earth-abundant transition metals due to their ready availability, economic advantage, and novel properties. In this case, manganese, the third most abundant transition-metal in Earth's crust, emerged as one leading competitors. Accordingly, a large number molecularly-defined Mn-complexes been synthesized employed for hydrogenation, dehydrogenation, hydroelementation reactions. regard, catalyst design is based three pillars, namely, metal-ligand bifunctionality, ligand hemilability, redox activity. Indeed, developed catalysts not only differ chelating atoms they possess but also working principles, thereby different turnover numbers product molecules. Hence, critical assessment molecularly defined manganese terms atoms, reaction conditions, mechanistic pathway, significant. Herein, we analyze complexes catalytic activity, versatility allow multiple transformations routes convert substrates target This article will be helpful get significant insight into design, aiding design.

Language: Английский

Citations

158

Development of a practical non-noble metal catalyst for hydrogenation of N-heteroarenes DOI
Veronica Papa, Yi-Xuan Cao,

Anke Spannenberg

et al.

Nature Catalysis, Journal Year: 2020, Volume and Issue: 3(2), P. 135 - 142

Published: Jan. 6, 2020

Language: Английский

Citations

155

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

Cleavage of Si–H, B–H, and C–H Bonds by Metal–Ligand Cooperation DOI
Takuya Higashi, Shuhei Kusumoto, Kyoko Nozaki

et al.

Chemical Reviews, Journal Year: 2019, Volume and Issue: 119(18), P. 10393 - 10402

Published: Aug. 13, 2019

Metal–ligand cooperation, in which metal and ligand participate bond cleavage formation, is gathering great attention recent years. In contrast to the classical by active centers with spectator ligands, metal–ligand cooperation has enabled unprecedented reactivities. Especially, cooperative H–H been extensively studied applied various catalysts. On other hand, there are substantial efforts expand scope of be cleaved than bond. This review summarizes progress cleavages Si–H, B–H, C–H bonds their catalytic applications.

Language: Английский

Citations

129

Manganese(I)‐Catalyzed β‐Methylation of Alcohols Using Methanol as C1 Source DOI Creative Commons
Akash Kaithal, Pit van Bonn, Markus Hölscher

et al.

Angewandte Chemie International Edition, Journal Year: 2019, Volume and Issue: 59(1), P. 215 - 220

Published: Oct. 25, 2019

Highly selective β-methylation of alcohols was achieved using an earth-abundant first row transition metal in the air stable molecular manganese complex [Mn(CO)

Language: Английский

Citations

111

Recent Progress with Pincer Transition Metal Catalysts for Sustainability DOI Open Access
Luca Piccirilli, Danielle L. J. Pinheiro, Martin Nielsen

et al.

Catalysts, Journal Year: 2020, Volume and Issue: 10(7), P. 773 - 773

Published: July 11, 2020

Our planet urgently needs sustainable solutions to alleviate the anthropogenic global warming and climate change. Homogeneous catalysis has potential play a fundamental role in this process, providing novel, efficient, at same time eco-friendly routes for both chemicals energy production. In particular, pincer-type ligation shows promising properties terms of long-term stability selectivity, as well allowing mild reaction conditions low catalyst loading. Indeed, pincer complexes have been applied plethora chemical processes, such hydrogen release, CO2 capture conversion, N2 fixation, biomass valorization synthesis high-value fuels. work, we show main advances last five years use transition metal key catalytic processes aiming more

Language: Английский

Citations

97