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Synfacts 2023; 19(08): 0775
DOI: 10.1055/s-0042-1752815
Metals in Synthesis

Leveraging Strain-Release in Dearomative Photocycloadditions of Bicyclic Aza-Arenes

Contributor(s):
Mark Lautens
,
Jonathan Bajohr
Kleinmans R, Dutta S, Ozols K, Shao H, Schäfer F, Thielemann R.-E, Chan HT, Daniliuc CG, Houk KN, *, Glorius F. * University of California, Los Angeles, USA and Westfälische Wilhelms-Universität Münster, Germany
ortho-Selective Dearomative [2π + 2σ] Photocycloadditions of Bicyclic Aza-Arenes.

J. Am. Chem. Soc. 2023;
145: 12324-12332
DOI: 10.1021/jacs.3c02961.
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Key words

photocatalysis - iridium catalysis - cycloaddition

Significance

Dearomatization of (hetero)arene molecules is an ongoing goal in medicinal chemistry, as the increased three-dimensionality of the resulting molecules may have improved drug-like qualities. Glorius, Houk and co-workers report ­highly ortho-selective photocycloadditions of bi­cyclic heteroarenes, leveraging the strained bi­cyclo[1.1.0]butanes as reactive partners to generate highly functionalized, medicinally-relevant molecular scaffolds.


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Comment

The authors ruled out thermal background reactivity by performing the reaction in MeCN at 100 °C. DFT studies are in support of an EnT mechanism; however, additional studies are underway to elucidate other productive pathways which may be operative.


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Publication History

Article published online:
14 July 2023

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