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Published May 16, 2022 | Supplemental Material
Journal Article Open

Photoredox Catalysis Mediated by Tungsten(0) Arylisocyanides in 1,2-Difluorobenzene

Abstract

We have studied the photochemical cyclization of 1-(2-iodobenzyl)-pyrrole (IBP) and 1-(2-bromobenzyl)-pyrrole (BBP) to 5H-pyrrolo[2,1-a]isoindol catalyzed by W(CNDipp)₆ (CNDipp = 2,6-diisopropylphenylisocyanide) in 1,2-difluorobenzene (DFB). Irradiation (445 nm) of W(CNDipp)₆ (5 mol %) in DFB solution converted 78% of IBP (50 mM) to product after 1 h (16 turnovers). Addition of tetra-n-butyl ammonium hexafluorophosphate (TBAPF₆) (0.2 M) to the DFB solution led to rapid photoinduced disappearance of W(CNDipp)₆ but, remarkably, did not inhibit photochemical cyclization of IBP, indicating that IBP cyclization could be driven by a nonluminescent photocatalyst.

Additional Information

© 2022 American Chemical Society. Received 3 December 2021. Published online 29 April 2022. Published in issue 16 May 2022. We thank Javier Fajardo, Jr. for helpful discussions. We thank the National Science Foundation (Grant CHE-1763429) and the Caltech Beckman Institute Laser Resource Center supported by the Arnold and Mabel Beckman Foundation. A.T.B. acknowledges a National Science Foundation Graduate Research Fellowship (NSF Grant No. DGE-1745301). Author Contributions. All authors have given approval to the final version of the manuscript. The authors declare no competing financial interest.

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Additional details

Created:
August 22, 2023
Modified:
October 24, 2023