Pivalophenone imine as a benzonitrile surrogate for directed C–H bond functionalization
Pivalophenone N–H imine has been found to serve as a prominent substrate for directed C–H alkylation and arylation reactions with alkyl bromides and aryl chlorides, respectively, under cobalt–N-heterocyclic carbene (NHC) catalysis. Unlike the case of the parent pivalophenone imine, the increased ste...
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| Main Authors: | , |
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| Other Authors: | |
| Format: | Article |
| Language: | English |
| Published: |
2018
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| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/86808 http://hdl.handle.net/10220/44261 |
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| Institution: | Nanyang Technological University |
| Language: | English |
| Summary: | Pivalophenone N–H imine has been found to serve as a prominent substrate for directed C–H alkylation and arylation reactions with alkyl bromides and aryl chlorides, respectively, under cobalt–N-heterocyclic carbene (NHC) catalysis. Unlike the case of the parent pivalophenone imine, the increased steric bulk of the resulting ortho-substituted pivalophenone imines allows them to undergo clean imine-to-nitrile conversion under peroxide photolysis or aerobic copper catalysis conditions. Overall, these two-step transformations offer convenient synthetic methods for ortho-functionalized benzonitriles. |
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