Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 10, Pages 6807-6811Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c00498
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Funding
- Shanghai Institute of Materia Medica
- Chinese Academy of Sciences
- National Natural Science Foundation of China [22171276, 21920102003]
- Youth Innovation Promotion Association CAS [2014229, 2018293]
- Institutes for Drug Discovery and Development, Chinese Academy of Sciences [CASIMM0120163006]
- Science and Technology Commission of Shanghai Municipality [17JC1405000, 21ZR1475400, 18431907100]
- Program of Shanghai Academic Research Leader [19XD1424600]
- National Science & Technology Major Project Key New Drug Creation and Manufacturing Program, China [2018ZX09711002-006]
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In this study, we report the synthesis of 1,3-enynes through palladium-catalyzed cross-coupling between enone derivatives and alkynylsilanes. The use of an appropriate pyridine-oxazoline ligand is crucial for achieving C-C cleavage and high E/Z stereoselectivity. This method demonstrates broad substrate scope, wide functional-group tolerance, and moderate-to-good yields. Furthermore, the late-stage diversification of natural product beta-ionone showcases the synthetic utility of this protocol.
We report herein the synthesis of 1,3-enynes via palladium-catalyzed cross-coupling between enone derivatives and alkynylsilanes. The employment of an appropriate pyridine-oxazoline ligand is the key to the C-C cleavage and the high E/Z stereoselectivity. This protocol features broad substrate scope and wide functional-group tolerance, affording the desired products in moderate-to-good yields. Late-stage diversification of natural product beta-ionone further demonstrated the synthetic utility of this protocol.
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