81245-50-3Relevant academic research and scientific papers
Formation of trisubstituted buta-1,3-dienes and α,β-unsaturated ketonesviathe reaction of functionalized vinyl phosphates and vinyl phosphordiamidates with organometallic reagents
Dvo?áková, Hana,Koudelka, Jakub,Oeser, Petr,Tobrman, Tomá?
, p. 35109 - 35120 (2020/10/19)
We studied the reactions of vinyl phosphates and vinyl phosphordiamidates containing an ester functional group with organometallic reagents. We found that the functionalized vinyl phosphates were smoothly converted into tri- and tetrasubstituted buta-1,3-
Synthesis of conjugated dienes and polyenes via diethyl phosphite promoted carbonyl olefination
Wang, Ru,Zhang, Songlin
, p. 39497 - 39507 (2014/11/08)
A protocol has been developed for the synthesis of conjugated dienes and polyenes from unsaturated carbonyl compounds and Grignard reagents in the presence of diethyl phosphite. This reaction was conveniently carried out under mild conditions in a one-pot fashion with moderate to good yields.
Selective arylation and vinylation at the α position of vinylarenes
Zou, Yinjun,Qin, Liena,Ren, Xinfeng,Lu, Yunpeng,Li, Yongxin,Zhou, Jianrong
supporting information, p. 3504 - 3511 (2013/07/05)
In intermolecular Heck reactions of styrene and vinylarenes, the aryl and vinyl groups routinely insert at the β position. However, selective insertion at the α position has been very rare. Herein, we provide a missing piece in the palette of Heck reaction, which gave >20:1 α selectivity. The key to our success is a new ferrocene 1,1′-bisphosphane (dnpf) that carries 1-naphthyl groups. Our mechanistic studies revealed that the high α selectivity is partly attributable to the steric effect of dnpf. The rigid and bulky 1-naphthyl groups of dnpf sterically disfavor β insertion. What the Heck! In intermolecular Heck reactions, insertion at the β position of aromatic olefins is very common, but reversal of the selectivity for selective α insertion has been a longstanding problem. A general method to couple aryl and vinyl triflates with aromatic olefins in >20:1 α selectivity is presented. The key to this successful approach is a new ferrocene bisphosphane with naphthyl groups on the phosphorus atom (see scheme; OTf=triflate). Copyright
