C1-取代的氧杂双环[2,2,1]庚-2,5-二烯-2,3-二羧酸酯的区域选择性钯催化开环反应

Edmunds Michael, Raheem Mohammed Abdul, Boutin Rebecca, Tait Katrina, Tam William

Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry and Biochemistry, University of Guelph, Guelph, Ontario, N1G 2W1, Canada.

Beilstein J Org Chem. 2016 Feb 9;12:239-44. doi: 10.3762/bjoc.12.25. eCollection 2016.

Palladium-catalyzed ring-opening reactions of C1 substituted 7-oxanorbornadiene derivatives with aryl iodides were investigated. The optimal conditions for this reaction were found to be PdCl2(PPh3)2, ZnCl2, Et3N and Zn in THF. Both steric and electronic factors played a role in the outcome of the reaction as increasing the steric bulk on the bridgehead carbon decreased the yield. These reactions were found to be highly regioselective, giving only one of the two possible regioisomers in all cases. A diverse collection of novel, highly substituted biphenyl derivatives were obtained.

研究了钯催化的C1取代的7-氧杂降冰片二烯衍生物与芳基碘的开环反应。发现该反应的最佳条件是在四氢呋喃中使用二氯二（三苯基膦）钯、氯化锌、三乙胺和锌。空间和电子因素在反应结果中都起作用，因为桥头碳上空间位阻的增加会降低产率。发现这些反应具有高度的区域选择性，在所有情况下只给出两种可能的区域异构体中的一种。得到了一系列多样的新型、高度取代的联苯衍生物。