Recent advances in directed C–H functionalizations using monodentate nitrogen-based directing groups

Organic Chemistry Frontiers, Journal Year: 2014, Volume and Issue: 1(7), P. 843 - 843

Published: May 14, 2014

The use of directing groups has proven to be a successful strategy enhance reactivity and control selectivity in C–H functionalization reactions. In the past decade, multitude new transformations have been explored, several recent reviews discussed group approaches for functionalization. This review focuses specifically on monodentate nitrogen-based published during two years, with aim covering body literature that is complementary existing reviews.

Language: Английский

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Amide-directed photoredox-catalysed C–C bond formation at unactivated sp3 C–H bonds

Nature, Journal Year: 2016, Volume and Issue: 539(7628), P. 272 - 275

Published: Oct. 12, 2016

Language: Английский

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Innate and Guided C–H Functionalization Logic

Accounts of Chemical Research, Journal Year: 2011, Volume and Issue: 45(6), P. 826 - 839

Published: Oct. 21, 2011

The combustion of organic matter is perhaps the oldest and most common chemical transformation utilized by mankind. generation a C–O bond at expense C–H during this process may be considered basic form functionalization. This illustrates extreme generality term "C–H functionalization", because it can describe conversion literally any into C–X (X being anything except H). Therefore, use to distinguish between what, in our view, are two distinct categories functionalization logic: "guided" "innate". Guided functionalizations, as name implies, guided external reagents or directing groups (covalently fleetingly bound) install new functional specifically targeted bonds. Conversely, innate functionalizations broadly defined reactions that exchange bonds for based solely on natural reactivity patterns absence other forces.Two substrates illustrate distinction dihydrojunenol isonicotinic acid. processes hydroxylation arylation, respectively, take place multiple locations each molecule. Innate lead substitution dictated inherent bias (steric electronic) substrate undergoing cleavage, whereas controlled forces such metal complexation steric reagent. Although not always clear cases do fit neatly single category, useful convention consider when analyzing strategies synthesis. We must emphasize although completely rigorous practical, we have nonetheless found tool planning stage synthesis.In Account, trace own studies area synthesis through lens "innate" descriptors. show how harnessing beneficial achieving unique constructions heterocycles carbonyl compounds, enabling rapid scalable total syntheses. were used synergistically create an entire family terpenes fashion. continue with discussion complex alkaloids high nitrogen content, which required invention uniquely chemoselective protocol. These findings led us develop series forging C–C interest largest body practicing chemists: medicinal chemists. Strategic logic dramatically positive effect efficiency synthesis, whether innate.

Language: Английский

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CH Activation: A Complementary Tool in the Total Synthesis of Complex Natural Products

Chemistry - A European Journal, Journal Year: 2012, Volume and Issue: 18(31), P. 9452 - 9474

Published: June 26, 2012

Abstract The recent advent of transition‐metal mediated CH activation is revolutionizing the synthetic field and gradually infusing a “CH mind‐set” in both students practitioners organic synthesis. As powerful testament this emerging tool, applications context total synthesis complex natural products are beginning to blossom. Herein, recently completed syntheses showcasing creative ingenious incorporation as strategic manoeuver compared with their “non‐CH activation” counterparts, illuminating new paradigm design.

Language: Английский

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Developing Ligands for Palladium(II)-Catalyzed C–H Functionalization: Intimate Dialogue between Ligand and Substrate

The Journal of Organic Chemistry, Journal Year: 2013, Volume and Issue: 78(18), P. 8927 - 8955

Published: April 8, 2013

Homogeneous transition-metal-catalyzed reactions are indispensable to all facets of modern chemical synthesis. It is thus difficult imagine that for much the early 20th century, reactivity and selectivity known homogeneous metal catalysts paled in comparison their heterogeneous biological counterparts. In intervening decades, advances ligand design bridged this divide, such today some most demanding bond-forming events mediated by ligand-supported species. While has propelled many areas catalysis, field Pd(II)-catalyzed C-H functionalization, suitable scaffolds lacking, which hampered development broadly practical transformations based on functionalization logic. Perspective, we offer an account our research employing three scaffolds, mono-N-protected amino acids, 2,6-disubstituted pyridines, 2,2'-bipyridines, address challenges posed several synthetically versatile substrate classes. Drawing work, discuss principles design, as need match a particular class, how traits tunability modularity can be advantageous reaction discovery.

Language: Английский

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