期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 351, 期 11-12, 页码 1897-1904出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200900334
关键词
alkynes; cyanation; oxygen; palladium
资金
- Inohana Foundation
A stereoselective 1,2-dicyanation of various alkynes in the presence of trimethylsilyl cyanide (TMSCN) by palladium(II) catalysis under aerobic conditions is investigated. This reaction includes two cyanation pathways, syn- and anti-cyanopalladation to alkynes that are activated by Pd(II). High syn-selectivity was observed in the reaction using terminal alkynes that have bulky substituents at a propargyl position and aliphatic internal alkynes. Furthermore, a dramatic acceleration was observed with substrates having an N-arenesulfonyl functionality at a propargyl position, this indicates that both sulfoxide and carbon-carbon triple bond act as Lewis bases to Pd(II).
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