Journal
ACS CATALYSIS
Volume 11, Issue 17, Pages 10789-10795Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.1c02533
Keywords
[3+2] cyclization; alpha-aryl-alpha-diazoester; terminal alkyne; cooperative catalysis; palladium
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Funding
- National Natural Science Foundation of China [21573032, 21602026]
- LiaoNing Revitalization Talents Program [XLYC1802030]
- Natural Science Foundation of Liaoning, China [2019JH3/30100001]
- Fundamental Research Funds for the Central Universities [DUT20LK42]
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Palladium and acid cooperative catalysis was proposed as a strategy for the [3 + 2] cycloaddition of acceptor/donor-type diazo compounds with terminal alkynes, resulting in high yields of 2,3,5-trisubstituted furans. This method provides an efficient pathway to prepare furan-containing organosilane and organoboron reagents, while preserving important functional groups during the cycloaddition reaction.
Palladium and acid cooperative catalysis is presented as a strategy for the [3 + 2] cycloaddition of acceptor/donor-type diazo compounds with terminal alkynes. The [3 + 2] cycloaddition of alpha-aryl-alpha-diazoacetates with terminal alkynes proceeded smoothly to produce 2,3,5-trisubstituted furans with high yields. This synthesis method provided a direct and efficient pathway to prepare furan ring-containing organosilane and organoboron reagents. Synthetically valuable functional groups such as chloro and bromo atoms, methoxycarbonyl, and carbonyl remained intact during the [3 + 2] cycloaddition reaction.
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