期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 139, 期 50, 页码 18307-18312出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b10009
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资金
- PCSIRT
- NSFC [21325208, 21572212]
- MOST [2017YFA0303500]
- FRFCU
- CAS [XDB20000000]
The palladium-catalyzed Mizoroki-Heck reaction is arguably one of the most significant carbon-carbon bond-construction reactions to be discovered in the last 50 years, with a tremendous number of applications in the production of chemicals. This Nobel-Prize-winning transformation has yet to overcome the obstacle of its general application in a range of alkyl electrophiles, especially tertiary alkyl halides that possess eliminable beta-hydrogen atoms. Whereas most palladium-catalyzed cross-coupling reactions utilize the ground-state reactivity of palladium complexes under thermal conditions and generally apply a single ligand system, we report that the palladium-catalyzed Heck reaction proceeds smoothly at room temperature with a variety of tertiary, secondary, and primary alkyl bromides upon irradiation with blue light-emitting diodes in the presence of a dual phosphine ligand system. We rationalize that this unprecedented transformation is achieved by utilizing the photoexcited-state reactivity of the palladium complex to enhance oxidative addition and suppress undesired beta-hydride elimination.
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