Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 26, Pages 6776-6780Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201403410
Keywords
allylic alcohol; allylic alkylation; DFT calculation; organocatalysis; palladium
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Funding
- National Natural Science Foundation of China [21172143, 21172145, 21372152, 21232004]
- Nippon Chemical Industrial Co., Ltd
- Shanghai Jiao Tong University
- CAMPUS Asia Program of Tohoku University
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Allylic alcohols were directly used in Pd-catalyzed allylic alkylations of simple ketones under mild reaction conditions. The reaction proceeded smoothly at 20 degrees C by the concerted action of a Pd catalyst, a pyrrolidine co-catalyst, and a hydrogen-bonding solvent, and does not require any additional reagents. A computational study suggested that methanol plays a crucial role in the formation of the pi-allylpalladium complex by lowering the activation barrier.
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