Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2019, Issue 9, Pages 1952-1956Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201900118
Keywords
Cycloheptene; Gold catalysis; Cyclopropene; Ring expansion; Alkynylbenzaldehyde
Categories
Funding
- NSFC [21402106]
- SRF for ROCS, SEM [20141685]
- Shandong Natural Science Foundation [ZR2018JL013, ZR2018MB014, ZR2014BQ024]
- Higher Educational Science and Technology Program [J15LA02]
- Qufu Normal University for Research Start-up Foundation
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A novel gold(III) and TfOH-cocatalyzed reaction of ortho-alkynylbenzaldehydes with cyclopropenes was described for the synthesis of a variety of functionalized benzo[7]annulene derivatives in a highly stereoselective manner. This reaction could undergo tandem [4+2] cycloaddition/ring expansion to achieve the construction of seven-membered-carbocycles, along with the cleavage of double bond of cyclopropenes. The reaction features simple operations, commercially available catalysts and broad substrate scope with good efficiencies.
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