Abstract
The direct α-arylation of carbonyl compounds using aryl halides represents a powerful method to synthesize critical building blocks for diverse useful compounds. Numerous synthetic methods exist to forge C(sp 2)–C(sp 3) bonds although mild and metal-free direct α-arylation of ketones remains a challenging transformation. Here we report a green-light-mediated α-arylation of ketones from readily available aryl halides via activation of a C(sp 2)–X bond (X = I, Br, Cl) and an α-carbonyl C(sp 3)–H bond in a single photocatalytic cycle. This approach is characterized by its mild reaction conditions, operational simplicity and wide functional group tolerance. Importantly, the impressive outcome of the multigram photocatalytic reaction underpins the strength of this method as a potentially practical and attractive approach for scale-up industrial purposes. The utility and scope of this reaction were further demonstrated by formal syntheses of several feedstock chemicals that are commercially expensive but critical for synthesizing numerous pharmaceutical agents. [Figure not available: see fulltext.]
Original language | English (US) |
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Pages (from-to) | 147-157 |
Number of pages | 11 |
Journal | Nature Synthesis |
Volume | 1 |
Issue number | 2 |
DOIs | |
State | Published - Feb 2022 |
ASJC Scopus subject areas
- Chemistry (miscellaneous)
- Inorganic Chemistry
- Organic Chemistry
- Materials Chemistry
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CCDC 2085197: Experimental Crystal Structure Determination
Hossain, M. M. (Contributor), Shaikh, A. C. (Contributor), Moutet, J. (Contributor) & Gianetti, T. L. (Contributor), Cambridge Crystallographic Data Centre, 2021
DOI: 10.5517/ccdc.csd.cc27ztfh, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc27ztfh&sid=DataCite
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CCDC 2085196: Experimental Crystal Structure Determination
Hossain, M. M. (Contributor), Shaikh, A. C. (Contributor), Moutet, J. (Contributor) & Gianetti, T. L. (Contributor), Cambridge Crystallographic Data Centre, 2021
DOI: 10.5517/ccdc.csd.cc27ztdg, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc27ztdg&sid=DataCite
Dataset