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Bifunctional Ligand Enables Efficient Gold‐Catalyzed Hydroalkenylation of Propargylic Alcohol
Authors:Dr. Shengrong Liao  Dr. Alessio Porta  Xinpeng Cheng  Xu Ma  Prof. Dr. Giuseppe Zanoni  Prof. Dr. Liming Zhang
Affiliation:1. http://www.chem.ucsb.edu/~zhang/index.html;2. Key Laboratory of Tropical Marine Bio-resources and Ecology, South China Sea Institute of Oceanology, CAS, Guangzhou, P. R. China;3. Department of Chemistry and Biochemistry, UCSB, Santa Barbara, CA, USA;4. Dept of Chem., Univ. of Pavia, Pavia, Italy
Abstract:Using the previously designed biphenyl‐2‐ylphosphine ligand, featuring a remote tertiary amino group, the first gold‐catalyzed intermolecular hydroalkenylation of alkynes has been developed. Synthetically valuable conjugated dienyl alcohols are formed in moderate to good yields. A range of alkenyltrifluoroborates are allowed as the alkenyl donor, and no erosion of alkene geometry and/or the propargylic configuration are detected. DFT calculations confirm the critical role of the remote basic group in the ligand as a general‐base catalyst for promoting this novel gold catalysis with good efficiency.
Keywords:conjugation  gold  ligand design  reaction mechanisms  synthetic methods
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