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Visible-Light Photo-Arbuzov Reaction of Aryl Bromides and Trialkyl Phosphites Yielding Aryl Phosphonates

Shaikh, Rizwan S., Düsel, Simon J. S., König, Burkhard·2016·ACS Catalysis

Abstract

Aryl phosphonates are functional groups frequently found in pharmaceutical and crop protection agents. For their synthesis via C–P bond formation typically transition-metal-catalyzed reactions are used. We report a visible-light photo-Arbuzov reaction as an efficient, mild, and metal-free alternative. Rhodamine 6G (Rh.6G) is used as the photocatalyst, generating aryl radicals under blue light. Coupling of the radicals with a wide range of trivalent phosphites gives aryl phosphonates in good to very good isolated yields. The mild reaction conditions allow the introduction of a phosphonate group into complex and sensitive pharmaceutically active molecules such as benzodiazepams and nicergoline by the activation of a carbon–halogen bond.

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Metadata

Authors
Shaikh, R. S., Düsel, S. J. S., & König, B.
Venue
ACS Catalysis
Published
2016-11-21
Volume
6
Issue
12
Pages
8410-8414
ISSN
2155-5435 (ISSN-L)
OpenAlex
W2550192427
Cited by
188
References
1
FWCI
8.32
Type
journal article
Language
en
Open access
closed

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CoChat. (2026). Citation check: Visible-Light Photo-Arbuzov Reaction of Aryl Bromides and Trialkyl Phosphites Yielding Aryl Phosphonates. https://app.cochat.ai/papers/10.1021/acscatal.6b02591
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Shaikh, R. S., Düsel, S. J. S., & König, B. (2016). Visible-Light Photo-Arbuzov Reaction of Aryl Bromides and Trialkyl Phosphites Yielding Aryl Phosphonates. ACS Catalysis. https://doi.org/10.1021/acscatal.6b02591

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