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124882 |
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|a dc
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|a Lecomte, Morgan
|e author
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|a Massachusetts Institute of Technology. Department of Chemistry
|e contributor
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|a Lipshultz, Jeffrey M.
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|a Kim-Lee
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|a Li, Gen
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|a Radosevich, Alexander T.
|e author
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|a Driving Recursive Dehydration by PIII/PV Catalysis: Annulation of Amines and Carboxylic Acids by Sequential C-N and C-C Bond Formation
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|b American Chemical Society (ACS),
|c 2020-04-27T17:26:52Z.
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|z Get fulltext
|u https://hdl.handle.net/1721.1/124882
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|a A method for the annulation of amines and carboxylic acids to form pharmaceutically relevant azaheterocycles via organophosphorus PIII/PV redox catalysis is reported. The method employs a phosphetane catalyst together with a mild bromenium oxidant and terminal hydrosilane reductant to drive successive C-N and C-C bond-forming dehydration events via the serial action of a catalytic bromophosphonium intermediate. These results demonstrate the capacity of PIII/PV redox catalysis to enable iterative redox-neutral transformations in complement to the common reductive driving force of the PIII/PV couple. ©2019
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|a NIH NIGMS (grant no. GM114547)
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|a Colloid and Surface Chemistry
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|a Biochemistry
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|a General Chemistry
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|a Catalysis
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|a Article
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|t 10.1021/jacs.9b06277
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|t Journal of the American Chemical Society
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