Advances in One-Pot Synthesis through Borrowing Hydrogen Catalysis

Chemical Reviews, Год журнала: 2018, Номер 118(4), С. 1410 - 1459

Опубликована: Янв. 10, 2018

The borrowing hydrogen (BH) principle, also called auto-transfer, is a powerful approach which combines transfer hydrogenation (avoiding the direct use of molecular hydrogen) with one or more intermediate reactions to synthesize complex molecules without need for tedious separation isolation processes. strategy usually relies on three steps, (i) dehydrogenation, (ii) reaction, and (iii) hydrogenation, an excellent well-recognized process from synthetic, economic, environmental point view. In this context, objective present review give global overview topic starting those contributions published prior emergence BH concept most recent current research under term catalysis. Two main subareas (homogeneous heterogeneous catalysis) have been identified, subheadings based source electrophile (alkanes, alcohols, amines) considered. Then type bond being formed (carbon–carbon carbon heteroatom) has taken into account end-up reaction working in tandem metal-catalyzed hydrogenation/dehydrogenation step. completed advances asymmetric catalysis using strategy.

Язык: Английский

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First-Row Transition Metal (De)Hydrogenation Catalysis Based On Functional Pincer Ligands

Chemical Reviews, Год журнала: 2018, Номер 119(4), С. 2681 - 2751

Опубликована: Дек. 31, 2018

The use of 3d metals in de/hydrogenation catalysis has emerged as a competitive field with respect to "traditional" precious metal catalyzed transformations. introduction functional pincer ligands that can store protons and/or electrons expressed by metal-ligand cooperativity and ligand redox-activity strongly stimulated this development conceptual starting point for rational catalyst design. This review aims at providing comprehensive picture the utilization first-row transition hydrogenation dehydrogenation related synthetic concepts relying on these such hydrogen borrowing methodology. Particular emphasis is put implementation relevance cooperating redox-active within mechanistic scenarios.

Язык: Английский

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3d-Metal Catalyzed N- and C-Alkylation Reactions via Borrowing Hydrogen or Hydrogen Autotransfer

Chemical Reviews, Год журнала: 2018, Номер 119(4), С. 2524 - 2549

Опубликована: Ноя. 20, 2018

The conservation of our element resources is a fundamental challenge mankind. development alcohol refunctionalization reactions possible fossil carbon strategy since alcohols can be obtained from indigestible and abundantly available biomass. rare noble metals, frequently used in key technologies such as catalysis, might feasible by replacing them with highly abundant metals. alkylation amines related C–C coupling are early examples reactions. These follow mostly the borrowing hydrogen or autotransfer catalysis concept, many 3d-metal catalysts have been disclosed recent years. In this review, we summarize progress made developing Cu, Ni, Co, Fe, Mn for C–N bond formation using concept. We expect that findings field will inspire others to develop new efficient selective earth-abundant metal applications novel mediated

Язык: Английский

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New Strategies for the Transition-Metal Catalyzed Synthesis of Aliphatic Amines

Chemical Reviews, Год журнала: 2020, Номер 120(5), С. 2613 - 2692

Опубликована: Фев. 17, 2020

Transition-metal catalyzed reactions that are able to construct complex aliphatic amines from simple, readily available feedstocks have become a cornerstone of modern synthetic organic chemistry. In light the ever-increasing importance across range chemical sciences, this review aims provide concise overview transition-metal approaches alkylamine synthesis and their functionalization. Selected examples amine bond forming include: (a) hydroamination hydroaminoalkylation, (b) C(sp3)–H functionalization, (c) visible-light-mediated photoredox catalysis.

Язык: Английский

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Catalytic (de)hydrogenation promoted by non-precious metals – Co, Fe and Mn: recent advances in an emerging field

Chemical Society Reviews, Год журнала: 2018, Номер 47(4), С. 1459 - 1483

Опубликована: Янв. 1, 2018

Catalytic hydrogenation and dehydrogenation reactions form the core of modern chemical industry. This vast class is found in any part synthesis starting from milligram-scale exploratory organic chemistry to multi-ton base chemicals production. Noble metal catalysis has long been key driving force enabling these transformations with carbonyl substrates their nitrogen-containing counterparts. review aimed at introducing reader remarkable progress made last three years development catalysts for hydrogenations dehydrogenative transformations.

Язык: Английский

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Manganese Complexes for (De)Hydrogenation Catalysis: A Comparison to Cobalt and Iron Catalysts

Angewandte Chemie International Edition, Год журнала: 2017, Номер 57(1), С. 46 - 60

Опубликована: Окт. 24, 2017

The sustainable use of the resources on our planet is essential. Noble metals are very rare and diversely used in key technologies, such as catalysis. Manganese third most abundant transition metal Earth's crust based recently discovered impressive reactivity hydrogenation dehydrogenation reactions, a potentially useful noble-metal "replacement". hope novel selectivity profiles, not possible with noble metals, also an aim manganese complexes (de)hydrogenation reactions was demonstrated for first time 2016. Herein, we summarize work that has been published since then especially discuss importance homogeneous catalysts comparison to cobalt iron catalysts.

Язык: Английский

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Key Green Chemistry research areas from a pharmaceutical manufacturers’ perspective revisited

Green Chemistry, Год журнала: 2018, Номер 20(22), С. 5082 - 5103

Опубликована: Янв. 1, 2018

The ACS Green Chemistry Institute® Pharmaceutical Roundtable has assembled an updated list of key research areas to highlight transformations and reaction media where more sustainable technologies would be most impactful.

Язык: Английский

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Homogeneous Catalysis by Cobalt and Manganese Pincer Complexes

ACS Catalysis, Год журнала: 2018, Номер 8(12), С. 11435 - 11469

Опубликована: Окт. 16, 2018

Homogeneous catalysis of organic transformations by metal complexes has been mostly based on noble metals. In recent years, tremendous progress made in the field base-metal catalysis, with pincer-type complexes, such as iron, cobalt, nickel, and manganese pincer systems. Particularly impressive is explosive growth Mn-based first being reported recently 2016. This review covers homogeneously catalyzed reactions using cobalt manganese. Various are described, including acceptorless dehydrogenation, hydrogenation, dehydrogenative coupling, hydrogen borrowing, transfer, H–X additions, C–C alkene polymerization N2 fixation, their scope brief mechanistic comments.

Язык: Английский

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Recent advances in homogeneous borrowing hydrogen catalysis using earth-abundant first row transition metals

Organic & Biomolecular Chemistry, Год журнала: 2018, Номер 17(7), С. 1595 - 1607

Опубликована: Сен. 17, 2018

The review highlights the recent advances (2013-present) in use of earth-abundant first row transition metals homogeneous borrowing hydrogen catalysis. utility catalysts based on Mn, Fe, Co, Ni and Cu to promote a diverse array important C-C C-N bond forming reactions is described, including discussion reaction mechanisms, scope limitations, future challenges this burgeoning area sustainable

Язык: Английский

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Sustainable Synthesis of Quinolines and Pyrimidines Catalyzed by Manganese PNP Pincer Complexes

Journal of the American Chemical Society, Год журнала: 2016, Номер 138(48), С. 15543 - 15546

Опубликована: Ноя. 22, 2016

This study represents the first example an environmentally benign, sustainable, and practical synthesis of substituted quinolines pyrimidines using combinations 2-aminobenzyl alcohols as well benzamidine two different alcohols, respectively. These reactions proceed with high atom efficiency via a sequence dehydrogenation condensation steps that give rise to selective C-C C-N bond formations, thereby releasing 2 equiv hydrogen water. A hydride Mn(I) PNP pincer complex recently developed in our laboratory catalyzes this process very efficient way. total 15 14 were synthesized isolated yields up 91 90%,

Язык: Английский

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