Arylation and vinylation of alkenes based on unusual sequential semipinacol rearrangement/Grob fragmentation of allylic alcohols.
Alkenes can be stereoselectively arylated and vinylated without transition-metal catalyst under mild conditions through an interesting NBS-promoted semipinacol rearrangement and a subsequent unusual NaOH-mediated Grob fragmentation.
Yuan
Dao-Yi
DY
State Key Laboratory of Applied Organic Chemistry and Department of Chemistry, Lanzhou University, Lanzhou 730000, PR China.
Tu
Yong-Qiang
YQ
Fan
Chun-An
CA
D000475:Alkenes / Q000737:chemistry*; D053138:Cyclohexenes; D006841:Hydrocarbons, Aromatic; D020005:Propanols / Q000737:chemistry*; D013237:Stereoisomerism; D014753:Vinyl Compounds
D000475:Alkenes; D053138:Cyclohexenes; D006841:Hydrocarbons, Aromatic; D020005:Propanols; D014753:Vinyl Compounds; C519041:semipinacol; C006463:allyl alcohol