Manganese‐Catalyzed Hydrofunctionalization of Alkenes

Carney, Jonathan R.; Dillon, Barry R.; Campbell, Leonie; Thomas, Stephen P.

doi:10.1002/ange.201805483

Cited by 21 publications

(3 citation statements)

References 54 publications

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“…Supporting Informationis available from the Wiley Online Library. The authors have cited additional references within the Supporting Information [33–38] …”

Section: Supporting Informationmentioning

confidence: 99%

Manganese Complex Catalyzed Sequential Multi‐component Reaction: Enroute to a Quinoline‐Derived Azafluorenes

Mondal,

Pal,

Phukan

et al. 2024

ChemSusChem

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The development of innovative synthetic strategies for constructing complex molecular structures is the heart of organic chemistry. This significance of novel reactions or reaction sequences would further enhance if they permitted the synthesis of new classes of structural motifs, which have not been previously created. The research on the synthesis of heterocyclic compounds is one of the most active topics in organic chemistry due to the widespread application of N‐heterocycles in life and material science. The development of a new catalytic process that employs first‐row transition metals to produce a range of heterocycles from renewable raw materials is considered highly sustainable approach. This would be more advantageous if done in an eco‐friendly and atom‐efficient manner. Herein we introduce, the synthesis of various new quinoline based azafluorenes via sequential dehydrogenative multicomponent reaction (MCR) followed by C(sp3)‐H hydroxylation and annulation. Our newly developed, Mn‐complexes have the ability to direct the reaction in order to achieve a high amount of desired functionalized heterocycles while minimizing the possibility of multiple side reactions. We also performed a series of control experiments, hydride trapping experiments, reaction kinetics, catalytic intermediate and DFT studies to comprehend the detailed reaction route and the catalyst's function in the MCR sequence.

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“…Supporting Informationis available from the Wiley Online Library. The authors have cited additional references within the Supporting Information [33–38] …”

Section: Supporting Informationmentioning

confidence: 99%

Manganese Complex Catalyzed Sequential Multi‐component Reaction: Enroute to a Quinoline‐Derived Azafluorenes

Mondal,

Pal,

Phukan

et al. 2024

ChemSusChem

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“…1b). [53][54][55][56][57][58] The reactions lead to linear or branched products depending upon the catalyst and the microenvironment of the reaction through the intermediacy of an Mn-hydride species formed via an ionic or radical mechanism. The dehydrogenative functionalization of alkenes leading to alkenyl silanes is a newer area of research (Fig.…”

Section: Introductionmentioning

confidence: 99%

“…Notably, the catalyst had to be highly selective to minimize the competitive hydroboration reactions. [53][54][55][56][57][58] Herein, we report the first example of a bench stable Mn(I)-complex catalyzed acceptorless dehydrogenative borylation (ABD) of alkenes with exclusive regio-and stereoselectivity and high chemoselectivity. The reaction operated under mild conditions without needing a hydrogen acceptor and delivered products in high yields.…”

Section: Introductionmentioning

confidence: 99%

Manganese catalyzed acceptorless dehydrogenative borylation of styrenes

Das

Kundu

Adhikari

et al. 2022

Preprint

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Alkenyl boronate esters are important synthons for various pharmaceuticals, agrochemicals, natural products, and material science. Direct alkene sp2 C-H bond borylation is highly valued for its synthesis. However, the drawbacks associated with chemo-, regio- and stereoselectivity, using late transition metal catalysts, and the need for sacrificial hydrogen scavengers impeded its practicability and sustainability. Herein, we utilized a 3d metal complex as a catalyst for synthesizing alkenyl boronate esters via the dehydrogenative coupling of styrenes and pinacolborane. Hydrogen gas is produced as the sole byproduct without needing an acceptor, making the process green and atom-economical. The methodology depicted excellent selectivity towards dehydrogenative borylation over direct hydroboration. Borylation of aromatic alkenes over aliphatic ones was also noticed. Derivatives of natural products and bioactive molecules underwent successful diversification. The product alkenyl boronate esters could be employed for synthesizing several drugs and potential anticancer agents. Thorough experimental and high-level computational studies were performed to delineate the reaction pathway. The hemilability and metal-ligand bifunctionality of the ligand backbone was found to be crucial for successful catalytic turnover.

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Recyclable Copper Nanoparticles‐Catalyzed Hydroboration of Alkenes and β‐Borylation of α,β‐Unsaturated Carbonyl Compounds with Bis(Pinacolato)Diboron

et al. 2021

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Nano‐ferrite‐supported Cu nanoparticles (Fe‐dopamine‐Cu NPs) catalyzed anti‐Markovnikov‐selective hydroboration of alkenes with B2pin2 is reported under mild reaction conditions. This protocol can be applied to a broad range of substrates with high functional group compatibility. In addition, we demonstrated the use of Fe‐dopamine‐Cu NPs as a catalyst for the β‐borylation of α,β‐unsaturated ketones and ester, providing alkylboronate esters in up to 98% yield. Reuse of the magnetically recyclable catalyst resulted in no significant loss of activity in up to five reaction runs for both systems.

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Manganese‐Catalyzed Hydrofunctionalization of Alkenes

Cited by 21 publications

References 54 publications

Manganese Complex Catalyzed Sequential Multi‐component Reaction: Enroute to a Quinoline‐Derived Azafluorenes

Manganese Complex Catalyzed Sequential Multi‐component Reaction: Enroute to a Quinoline‐Derived Azafluorenes

Manganese catalyzed acceptorless dehydrogenative borylation of styrenes

Recyclable Copper Nanoparticles‐Catalyzed Hydroboration of Alkenes and β‐Borylation of α,β‐Unsaturated Carbonyl Compounds with Bis(Pinacolato)Diboron

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