期刊
ORGANIC CHEMISTRY FRONTIERS
卷 8, 期 13, 页码 3366-3371出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1qo00330e
关键词
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资金
- National Natural Science Foundation of China [21702189, 21672193, 21272218]
- Key Scientific and Technological Project of Henan Province [202102310004]
- China Ministry of Industry and Information Technology [Z135060009002]
- 111 Project [D20003]
- China Postdoctoral Science Foundation [2017M610458, 2018T110737]
- Zhengzhou University of China
This study presents a new palladium/phosphine cooperative catalytic system for the synthesis of bicyclo[3.1.0]hexene derivatives, highlighting the crucial roles of both Pd and phosphine in the selective intermolecular activation of Morita-Baylis-Hillman carbonates. This strategy opens up a new avenue for efficient and economical metal/Lewis base dual catalytic systems and provides valuable clues on solving the limitations of selective activation.
Herein we report a new palladium/phosphine cooperative catalytic system for the synthesis of bicyclo[3.1.0]hexene derivatives, particularly useful structural motifs in numerous biologically active entities. By application of our palladium/phosphine cooperative catalytic system, we accomplish the first selective intermolecular activation of Morita-Baylis-Hillman carbonates, where the phosphine species leads to a zwitterionic allylic ylide and the Pd catalyst generates a pi-allylpalladium complex. Experimental results indicate that both the Pd and phosphine play crucial roles in the sequential annulation reaction. This strategy opens up a new avenue for efficient and economical metal/Lewis base dual catalytic systems and provides valuable clues on solving the limitations of selective activation.
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