Multimodal Acridine Photocatalysis Enables Direct Access to Thiols from Carboxylic Acids and Elemental Sulfur Article Swipe
Arka Porey
,
Seth O. Fremin
,
Sachchida Nand
,
Ramon Trevino
,
William Hughes
,
Shree Krishna Dhakal
,
Viet D. Nguyen
,
Samuel G. Greco
,
Hadi D. Arman
,
Oleg V. Larionov
·
YOU?
·
· 2024
· Open Access
·
· DOI: https://doi.org/10.26434/chemrxiv-2023-7wx16-v2
YOU?
·
· 2024
· Open Access
·
· DOI: https://doi.org/10.26434/chemrxiv-2023-7wx16-v2
Development of photocatalytic systems that facilitate mechanistically different steps in complex catalytic manifolds by distinct activation modes can enable previously inaccessible synthetic transformations. However, multimodal photocatalytic systems remain understudied, impeding their implementation in catalytic methodology. We report herein a photocatalytic access to thiols that directly merges the structural diversity of carboxylic acids with the ready availability of elemental sulfur without substrate preactivation. The photocatalytic transformation provides a direct radical-mediated segue to one of the most biologically important and synthetically versatile organosulfur functionalities, whose synthetic accessibility remains largely dominated by two-electron-mediated processes based on toxic and uneconomical reagents and precursors. The two-phase radical process is facilitated by a multimodal catalytic reactivity of acridine photocatalysis that enables both the singlet excited state PCET-mediated decarboxylative carbon–sulfur bond formation and the previously unknown radical reductive disulfur bond cleavage by a photoinduced HAT process in the silane–triplet acridine system. The study points to a significant potential of multimodal photocatalytic systems in providing new directions to previously inaccessible transformations.
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- Type
- preprint
- Language
- en
- Landing Page
- https://doi.org/10.26434/chemrxiv-2023-7wx16-v2
- https://chemrxiv.org/engage/api-gateway/chemrxiv/assets/orp/resource/item/65dfbc3ce9ebbb4db98286c2/original/multimodal-acridine-photocatalysis-enables-direct-access-to-thiols-from-carboxylic-acids-and-elemental-sulfur.pdf
- OA Status
- gold
- Cited By
- 2
- References
- 65
- Related Works
- 10
- OpenAlex ID
- https://openalex.org/W4392289483
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Raw OpenAlex JSON
- OpenAlex ID
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https://openalex.org/W4392289483Canonical identifier for this work in OpenAlex
- DOI
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https://doi.org/10.26434/chemrxiv-2023-7wx16-v2Digital Object Identifier
- Title
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Multimodal Acridine Photocatalysis Enables Direct Access to Thiols from Carboxylic Acids and Elemental SulfurWork title
- Type
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preprintOpenAlex work type
- Language
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enPrimary language
- Publication year
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2024Year of publication
- Publication date
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2024-02-29Full publication date if available
- Authors
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Arka Porey, Seth O. Fremin, Sachchida Nand, Ramon Trevino, William Hughes, Shree Krishna Dhakal, Viet D. Nguyen, Samuel G. Greco, Hadi D. Arman, Oleg V. LarionovList of authors in order
- Landing page
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https://doi.org/10.26434/chemrxiv-2023-7wx16-v2Publisher landing page
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https://chemrxiv.org/engage/api-gateway/chemrxiv/assets/orp/resource/item/65dfbc3ce9ebbb4db98286c2/original/multimodal-acridine-photocatalysis-enables-direct-access-to-thiols-from-carboxylic-acids-and-elemental-sulfur.pdfDirect link to full text PDF
- Open access
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YesWhether a free full text is available
- OA status
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goldOpen access status per OpenAlex
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https://chemrxiv.org/engage/api-gateway/chemrxiv/assets/orp/resource/item/65dfbc3ce9ebbb4db98286c2/original/multimodal-acridine-photocatalysis-enables-direct-access-to-thiols-from-carboxylic-acids-and-elemental-sulfur.pdfDirect OA link when available
- Concepts
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Photocatalysis, Sulfur, Acridine, Chemistry, Combinatorial chemistry, Photochemistry, Organic chemistry, CatalysisTop concepts (fields/topics) attached by OpenAlex
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2Total citation count in OpenAlex
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2024: 2Per-year citation counts (last 5 years)
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65Number of works referenced by this work
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10Other works algorithmically related by OpenAlex
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