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Rhodium(III)-Catalyzed Annulation of

Acetophenone O‑Acetyl Oximes with


Allenoates through Arene C−H
Activation: An Access to Isoquinolines
Adam Alber
2-9-2019
Progression
● Background

● Methods

● Mechanism

● Conclusion
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Goals
● Novel ways of developing isoquinoline derivatives
○ Pharmaceutical activity

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Methods of generation (previous)
● Co(III) catalyzed reaction
○ Requires Ag2CO3 as an external oxidant

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Proposed novel method
● Rh(III) catalyzed reaction
○ [4+2] annulation under redox-neutral conditions

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Optimization of conditions

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Optimization of acetophenone o-acetyl oximes

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Optimization of allenoates

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Mechanistic studies
● Deuterated pivalic acid used to deuterate acetophenone o-acetyl oxime

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Proposed Mechanism

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Conclusions
● Isoquinolines generated under redox-neutral conditions
○ Avoids using metal salts as external oxidants

● Regioselective and broad scoped

● Annulation of acetophenone o-acetyl oximes with allenoates further explored

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Reference
[1] Wang, Q.; Lou, J.; Huang, Z.; Yu, Z. The Journal of Organic Chemistry 2019.

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