期刊
ACS CATALYSIS
卷 9, 期 4, 页码 3213-3218出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.9b00248
关键词
alkynes; dimerization; cobalt; metallaphotoredox; macrocyclization
资金
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- Universite de Montreal
- Centre for Green Chemistry and Catalysis (CGCC)
A photochemical hydroalkynylation is reported employing a metallaphotoredox approach using cobalt catalysis and an organic dye, 4CzIPN. The protocol enables catalysis without the need for stoichiometric metal reductants, normally needed to convert higher oxidation state cobalt complexes to their more active lower oxidation states. The hydroalkynylation provides 1,3-enynes in good to high yields and E-selectivity (25-99% yield, 17 -> 99:1 E:Z, 27 examples). Importantly, cross-dimerizations of terminal alkynes that are typically rare are also possible and occur with unusually high levels of stereoselection. In addition, macrocyclic hydroalkynylations are reported in good to high yields, affording macrocyclic enyne motifs, which are found in numerous bioactive natural products
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