Visible Light Promoted Direct Deuteration of Alkenes via Co(III)–H Mediated H/D Exchange

Jia, Zongbin; Luo, Sanzhong

doi:10.31635/ccschem.022.202202476

Cited by 10 publications

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“…2 ). Previously, we found oxime-Co(III) catalyst 5a was able to promote the deuteration of styrene through [Co III ]-H mediated hydroalkylation-dehydrogenation process 29 . In contrast, 5b showed virtually no activity in the H/D exchange reaction (Fig.…”

Section: Resultsmentioning

confidence: 99%

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Asymmetric C–H Dehydrogenative Alkenylation via a Photo-induced Chiral α‑Imino Radical Intermediate

Jia,

Cheng,

Zhang

et al. 2024

Nat Commun

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The direct alkenylation with simple alkenes stands out as the most ideal yet challenging strategy for obtaining high-valued desaturated alkanes. Here we present a direct asymmetric dehydrogenative α-C(sp3)-H alkenylation of carbonyls based on synergistic photoredox-cobalt-chiral primary amine catalysis under visible light. The ternary catalytic system enables the direct coupling of β-keto-carbonyls and alkenes through a cooperative radical addition-dehydrogenation process involving a chiral α-imino radical and Co(II)-metalloradical intermediate. A catalytic H-transfer process involving nitrobenzene is engaged to quench in situ generated cobalt hydride species, ensuring a chemoselective alkenylation in good yields and high enantioselectivities.

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Section: Resultsmentioning

confidence: 99%

“…Hydrogen transfer with cobalt. [Co III ]-H species are known to undergo reversible addition-elimination with alkenes 24,29 . Under hydrogen-evolving conditions in the absence of H-acceptor, the reaction afforded mainly alkene-dimerization byproduct b1 (42% yield) (Fig.…”

Section: Mechanistic Studiesmentioning

confidence: 99%

Asymmetric C–H Dehydrogenative Alkenylation via a Photo-induced Chiral α‑Imino Radical Intermediate

Jia,

Cheng,

Zhang

et al. 2024

Nat Commun

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“…The H/D exchange of alkenes was achieved using an efficient homogeneous cobalt catalyst by Luo and co‐workers (Figure 4a). [ 25 ] In this work, four‐coordinated planar catalyst precursor cobalt chlorine was discovered to undergo single electron transfer and H/D exchange with D 2 O to form Co‐D species, successively. The Co‐D species can further react with olefins and generate thermodynamically stable deuterated alkenes after multiple rapid addition‐elimination processes.…”

Section: Hydrogen Isotope Exchangementioning

confidence: 99%

Recent Advances in Deuteration Reactions^†

Li,

Shabbir,

et al. 2024

Chin. J. Chem.

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Comprehensive SummaryThe deuteration of organic compounds has attracted more and more attentions in recent years for the potential applications in new drug discovery and synthetic chemistry. For this purpose, many efficient deuterium labeling methodologies have been developed, including hydrogen isotope exchange (HIE) reactions, reductive deuteration, and dehalogenative deuteration that allow for the synthesis of selectively deuterated compounds. In the last few years, great breakthroughs in selective isotope labeling have been achieved and the interest in new methodologies for the deuteration of organic molecules is rising. In this review, we summarized the recent developments in the selective deuteration of organic molecules since 2021. Several types of key processes in deuterium incorporation reactions, including H/D exchange, reductive deuteration and dehalogenative deuteration, are introduced and discussed.This article is protected by copyright. All rights reserved.

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“…2a). To meet the rising demand, 9 there is a great need for the practical construction of deuterated pharmaceuticals and their intermediates with good regioselectivity and deuterization rates attained by using a low-cost and sustainable deuterium source under mild conditions. 10…”

Section: Introductionmentioning

confidence: 99%

Highly effective and selective FeBr₃-promoted deuterium bromination/cyclization of 1,n-enynes

Li,

Du,

et al. 2024

Org. Biomol. Chem.

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Visible Light Promoted Direct Deuteration of Alkenes via Co(III)–H Mediated H/D Exchange

Cited by 10 publications

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Asymmetric C–H Dehydrogenative Alkenylation via a Photo-induced Chiral α‑Imino Radical Intermediate

Asymmetric C–H Dehydrogenative Alkenylation via a Photo-induced Chiral α‑Imino Radical Intermediate

Recent Advances in Deuteration Reactions^†

Highly effective and selective FeBr₃-promoted deuterium bromination/cyclization of 1,n-enynes

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Visible Light Promoted Direct Deuteration of Alkenes via Co(III)–H Mediated H/D Exchange

Cited by 10 publications

References 0 publications

Asymmetric C–H Dehydrogenative Alkenylation via a Photo-induced Chiral α‑Imino Radical Intermediate

Asymmetric C–H Dehydrogenative Alkenylation via a Photo-induced Chiral α‑Imino Radical Intermediate

Recent Advances in Deuteration Reactions†

Highly effective and selective FeBr3-promoted deuterium bromination/cyclization of 1,n-enynes

Contact Info

Product

Resources

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Recent Advances in Deuteration Reactions^†

Highly effective and selective FeBr₃-promoted deuterium bromination/cyclization of 1,n-enynes