One-step synthesis of indolizino[3,4,5-<i>ab</i>]isoindoles by manganese(<scp>i</scp>)-catalyzed C–H activation: structural studies and photophysical properties

Cembellín, Sara; Maisuls, Iván; Daniliuc, Constantin G.; Osthues, Helena; Doltsinis, Nikos L.; Strassert, Cristian A.; Glorius, Frank

doi:10.1039/d1ob02246f

Cited by 5 publications

(2 citation statements)

References 38 publications

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“…The formation of heterocycles in this manner is particularly interesting given their broad applicability in medicinal chemistry and agrochemistry . Photoinduced methods have proven to be an excellent tool for the construction of such complex organic backbones . In this context, the difunctionalization of alkenes provides the expedited generation of molecular complexity from simple chemical feedstocks with excellent atom economy.…”

Section: Introductionmentioning

confidence: 99%

Trifunctionalization of Cinnamyl Alcohols Provides Access to Brominated α,α-Difluoro-γ-lactones via a Photoinduced Radical–Polar–Radical Mechanism

et al. 2022

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A photochemical synthesis of brominated α,α-difluoro-γ-lactones from cinnamyl alcohols and ethyl bromodifluoroacetate is reported via one-pot Giese addition/lactonization/halogen-atom transfer (XAT) processes. This transformation provides brominated α,α-difluoro-γ-lactones in moderate to good diastereoselectivities. The reaction affords a rapid increase in molecular complexity in organofluorine chemical space. Dispersion-corrected density functional theory (DFT) calculations and experiments support a lactonization-induced radical chain mechanism in which a long-lived radical intermediate undergoes a diastereoselective halogen-atom transfer to restart the radical chain cycle.

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Section: Introductionmentioning

confidence: 99%

Trifunctionalization of Cinnamyl Alcohols Provides Access to Brominated α,α-Difluoro-γ-lactones via a Photoinduced Radical–Polar–Radical Mechanism

et al. 2022

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“…In this context, we envisioned the regioselective preparation of relevant 1,3-dienes exploiting our previous experience on manganese C–H activation and allene reactivity . Allenes, with two orthogonal CC double bonds, play an important role in transition-metal-catalyzed transformations thanks to the strong affinity of C–metal nucleophiles for π-bonds.…”

mentioning

confidence: 99%

Regioselectivity Control in the Synthesis of Linear Conjugated Dienes Enabled by Manganese(I)-Catalyzed C–H Activation

Matesanz,

Gamarra,

del Campo

et al. 2023

ACS Catal.

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A highly selective Mn(I)-catalyzed dienylation of arenes and heteroarenes with acetylated allenes is described. The reported transformation proceeds by a simple one-pot procedure and delivers linear 1,3-dienes as single products with high stereoselectivity and total regioselectivity. A great variety of allenic substrates bearing diverse substitution patterns can be applied in this protocol where the insertion step occurs at the terminal carbon of the allene coupling partner, in contrast with the former preparations of dienes through C–H activation. This practical strategy features wide functional group tolerance and preparative scale utility showing very good efficiency in the late-stage functionalization of complex valuable molecules. Furthermore, the synthetic importance of the method is highlighted by different derivatizations of the final products, which can exhibit interesting fluorescence properties.

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Recent Advances and Prospects in Manganese‐Catalyzed C−H Activation

Anusree,

Devi,

Anilkumar

2024

Adv Synth Catal

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C–H activation represents an interesting alternative to conventional cross‐coupling methods, avoiding the requirement of additional steps to introduce activating groups. Generally, Pd‐catalyzed reactions have been extensively employed for C–H activation. The high cost and limited availability of resources of Pd have prompted us to explore alternative transition metals. In this context, researchers are turning to Earth Abundant Metals (EAMs) like manganese and iron for their potential in C–H activation.Significant progress has been made in manganese‐catalyzed C–H activation in recent years, showcasing excellent specificity, environmental compatibility, and versatility across different substrates. This review summarizes approximately 50 recent publications highlighting significant advancements in this field from 2020 to 2023.

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One-step synthesis of indolizino[3,4,5-ab]isoindoles by manganese(i)-catalyzed C–H activation: structural studies and photophysical properties

Abstract: Herein, a regioselective synthesis of indolizino[3,4,5-ab]isoindoles (INIs), a valuable class of heterocycles with interesting luminescence properties, is described using manganese(I)-catalyzed C−H activation. The reported transformation proceeds in a one-step procedure...

Cited by 5 publications

References 38 publications

Trifunctionalization of Cinnamyl Alcohols Provides Access to Brominated α,α-Difluoro-γ-lactones via a Photoinduced Radical–Polar–Radical Mechanism

Trifunctionalization of Cinnamyl Alcohols Provides Access to Brominated α,α-Difluoro-γ-lactones via a Photoinduced Radical–Polar–Radical Mechanism

Regioselectivity Control in the Synthesis of Linear Conjugated Dienes Enabled by Manganese(I)-Catalyzed C–H Activation

Recent Advances and Prospects in Manganese‐Catalyzed C−H Activation

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