Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada M5S 3H6.
Org Lett. 2019 Sep 6;21(17):7163-7168. doi: 10.1021/acs.orglett.9b02797. Epub 2019 Aug 21.
A scalable, diastereoselective nickel-catalyzed carboiodination reaction is reported that avoids metal-based reducing agents. Novel -dihydroquinolones and previously unreported tetrahydroquinolines are now readily prepared. The generation of -dihydroquinolones is noteworthy, as this selectivity is opposite to that of the Pd variant. Mechanistic insight into the nature of the nickel-catalyzed carboiodination reaction was derived experimentally, suggesting a catalyst-controlled cyclization and stereoretentive reductive elimination.
报道了一种可扩展的、对映选择性的镍催化碳-碘键形成反应，该反应避免了使用金属还原剂。新型的二氢喹啉酮和以前未报道的四氢喹啉现在可以很容易地制备。值得注意的是，-二氢喹啉酮的生成具有选择性，这与钯变体的选择性相反。通过实验推导出了对镍催化碳-碘键形成反应本质的机理见解，表明这是一种催化剂控制的环化和立体保留的还原消除反应。
