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Abstract
Photoredox-catalyzed methylcyclobutanations of alkylboronic esters are described. The reactions proceed through single-electron transfer induced deboronative radical addition to an electron-deficient alkene followed by single-electron reduction and polar 4-exo-tet cyclization with a pendant alkyl halide. Key to the success of the methodology was the use of easily oxidizable arylboronate complexes. Structurally diverse cyclobutanes are shown to be conveniently prepared from readily available alkylboronic esters and a range of haloalkyl alkenes. The mild reactions display excellent functional group tolerance, and the radical addition-polar cyclization cascade also enables the synthesis of 3-, 5-, 6-, and 7-membered rings.
Original language | English |
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Pages (from-to) | 3870-3874 |
Number of pages | 5 |
Journal | Angewandte Chemie - International Edition |
Volume | 58 |
Issue number | 12 |
Early online date | 15 Feb 2019 |
DOIs | |
Publication status | Published - 18 Mar 2019 |
Keywords
- photoredox catalysis
- cyclobutanes
- boronic esters
- radical-polar crossover
- cascade
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Dive into the research topics of 'Photoredox-Catalyzed Cyclobutane Synthesis by a Deboronative Radical Addition–Polar Cyclization Cascade'. Together they form a unique fingerprint.Projects
- 2 Finished
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FRESCO: Efficient, Flexible Synthesis of Molecules with Tailored Shapes: from Photoswitchable Helices to anti-Cancer Compounds
Aggarwal, V. K. (Principal Investigator)
1/10/15 → 31/03/21
Project: Research
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Changing the Synthesis Landscape with Boron at the Helm: from Chiral Organometallics to Assembly Line Synthesis
Aggarwal, V. K. (Principal Investigator)
14/05/12 → 13/01/18
Project: Research