Cobalt()-catalyzed hydroarylation of 1,3-diynes and internal alkynes with picolinamides promoted by alcohol

The Co( ii )-catalyzed selective C-H alkenylation of picolinamides with 1,3-diynes has been developed. This protocol can be applied to a variety of 1,3-diynes. In addition, both symmetrical and unsymmetrical internal alkynes were well tolerated, affording the corresponding alkenyl arenes. Moreover,...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2020-11, Vol.56 (91), p.14231-14234
Hauptverfasser: Gao, Yuan, Zhang, Mengfan, Wang, Chaoyu, Yang, Zhen, Huang, Xianqiang, Feng, Ruokun, Qi, Chenze
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Sprache:eng
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Zusammenfassung:The Co( ii )-catalyzed selective C-H alkenylation of picolinamides with 1,3-diynes has been developed. This protocol can be applied to a variety of 1,3-diynes. In addition, both symmetrical and unsymmetrical internal alkynes were well tolerated, affording the corresponding alkenyl arenes. Moreover, control experiments indicated that C-H bond cleavage may be involved in the rate-determining step. Furthermore, a deuterium incorporation product was achieved when deuterated alcohol was employed as the solvent, which suggested that alcohol was essential for the final protonolysis. The Co( ii )-catalyzed selective C-H alkenylation of picolinamides with 1,3-diynes and internal alkynes for the synthesis of conjugated enynes and alkenyl arenes has been developed. The results of control experiments showed that alcohol was essential for the final protonolysis.
ISSN:1359-7345
1364-548X
DOI:10.1039/d0cc05616b