Asymmetric alkene–alkene reductive cross-coupling reaction<i>via</i>visible-light photoredox/cobalt dual catalysis

Maiti, Mamata; Jana, Sayan K.; Maji, Biplab

doi:10.1039/d3cc02792a

Cited by 2 publications

(1 citation statement)

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“…[52] With the concomitant rise in the above technology, great emphasis has been given to asymmetric carbon-carbon and carbon-heteroatom bond formation under photocatalytic conditions. [49,[53][54][55][56] In this context, the key step for the synthesis of chiral heterocycles is asymmetric carbon-heteroatom bond formation, which can be achieved under photocatalytic conditions. In 2016, an exciting review demonstrated a detailed view of visible-light-induced heterocycle synthesis and functionalization in the form of achiral version.…”

Section: Introductionmentioning

confidence: 99%

Photochemical Synthesis of Chiral Heterocycles via Asymmetric Carbon‐Heteroatom Bond Formation

Brijwashi Sharma,

Saha,

Mohan Guru

2024

Adv Synth Catal

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Chiral heterocyclic compounds play a crucial role in the pharmaceutical science, materials science, and agrochemical industries. The critical step for synthesizing chiral heterocycles is the formation of asymmetric carbon‐heteroatom bonds, which can be achieved in a chiral environment under thermal or photochemical conditions. However, photochemical asymmetric transformation has become an area of immense growth in the past 15 years. In the drug discovery and development era, chiral photochemical transformations have drawn the attention of researchers to develop new synthetic strategies for chiral heterocycles via asymmetric carbon‐heteroatom bond formation. Chiral photochemistry in the pathway of asymmetric synthesis requires a chirality source which is transferred to the products. A catalytic chiral metal complexing agent or a chiral photosensitizer that generally follows a single electron transfer (SET) or oxidative and reductive quenching cycle has been widely exploited to achieve this goal. In this review, we have demonstrated the recent development of photochemical synthesis of chiral heterocycles via asymmetric carbon‐heteroatom bond formation by using a chiral metal catalyst, asymmetric organocatalyst, or dual catalytic system based on their plausible mechanism.

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Section: Introductionmentioning

confidence: 99%

Photochemical Synthesis of Chiral Heterocycles via Asymmetric Carbon‐Heteroatom Bond Formation

Brijwashi Sharma,

Saha,

Mohan Guru

2024

Adv Synth Catal

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Blue‐Light Irradiated Mn(0)‐Catalyzed Hydroxylation and C(sp³)−H Functionalization of Unactivated Alkanes with C(sp²)−H Bonds of Quinones for Alkylated Hydroxy Quinones and Parvaquone

Kumar Jha,

Rohilla,

Jain

et al. 2024

Chemistry A European J

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Site‐selective C(sp3)‐H functionalization of unreactive hydrocarbons is always challenging due to its inherited chemical inertness, slightly different reactivity of various C‐H bonds, and intrinsically high bond dissociation energies. Here, we present a site‐selective C−H alkylation of naphthoquinone with unactivated hydrocarbons using Mn2(CO)10 as a catalyst under blue‐light (457 nm) irradiation without any external acid or base and pre‐functionalization. The selective C‐H functionalization of tertiary over secondary and secondary over primary C(sp3)−H bonds in abundant chemical feedstocks was achieved, and hydroxylation of quinones was realized in situ by employing the developed methodology. This protocol provides a new catalytic system for the direct construction of high‐value‐added compounds, namely, parvaquone (a commercially available drug, used to treat theileriosis) and its derivatives under ambient reaction conditions. Moreover, this operationally simple protocol applies to various linear‐, branched‐, and cyclo‐alkanes with high degrees of site selectivity under blue‐light conditions and could provide rapid and straightforward access to versatile methodologies for upgrading feedstock chemicals. Mechanistic insight by radical trapping, radical scavenging, EPR, and other controlled experiments well corroborated with DFT studies suggest that the reaction proceeds by a radical pathway.

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Asymmetric alkene–alkene reductive cross-coupling reactionviavisible-light photoredox/cobalt dual catalysis

Abstract: The first example of asymmetric alkene-alkene reductive coupling is demonstrated via visible-light-fueled photoredox/cobalt dual catalysis. The desymmetrization reaction provided products (>20 examples) with up to five chiral centers in single-step...

Cited by 2 publications

References 32 publications

Photochemical Synthesis of Chiral Heterocycles via Asymmetric Carbon‐Heteroatom Bond Formation

Photochemical Synthesis of Chiral Heterocycles via Asymmetric Carbon‐Heteroatom Bond Formation

Blue‐Light Irradiated Mn(0)‐Catalyzed Hydroxylation and C(sp³)−H Functionalization of Unactivated Alkanes with C(sp²)−H Bonds of Quinones for Alkylated Hydroxy Quinones and Parvaquone

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Asymmetric alkene–alkene reductive cross-coupling reactionviavisible-light photoredox/cobalt dual catalysis

Abstract: The first example of asymmetric alkene-alkene reductive coupling is demonstrated via visible-light-fueled photoredox/cobalt dual catalysis. The desymmetrization reaction provided products (>20 examples) with up to five chiral centers in single-step...

Cited by 2 publications

References 32 publications

Photochemical Synthesis of Chiral Heterocycles via Asymmetric Carbon‐Heteroatom Bond Formation

Photochemical Synthesis of Chiral Heterocycles via Asymmetric Carbon‐Heteroatom Bond Formation

Blue‐Light Irradiated Mn(0)‐Catalyzed Hydroxylation and C(sp3)−H Functionalization of Unactivated Alkanes with C(sp2)−H Bonds of Quinones for Alkylated Hydroxy Quinones and Parvaquone

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Blue‐Light Irradiated Mn(0)‐Catalyzed Hydroxylation and C(sp³)−H Functionalization of Unactivated Alkanes with C(sp²)−H Bonds of Quinones for Alkylated Hydroxy Quinones and Parvaquone