01869nas a2200241   4500008004100000022001400041245013600055210006900191260000800260300001200268490000600280520105500286653001701341653001901358653001201377653001401389653001101403653002901414100002201443700001801465700002001483856012401503       2019                        eng d  a2155-543500aNickel-catalyzed straightforward and regioselective C-H alkenylation of indoles with alkenyl bromides: scope and mechanistic aspect0 aNickelcatalyzed straightforward and regioselective CH alkenylati  cJAN  a431-4410 v93 a<p>Nickel-catalyzed regioselective C-H bond alkenylation of indoles and related heteroarenes with alkenyl bromides is accomplished under relatively mild conditions. This method allows the straightforward synthesis of C-2 alkenylated indoles employing an air-stable and well-defined nickel catalyst, (bpy)NiBr2, providing a solution to the limitations associated with hydroindolation and oxidative alkenylation. The reaction conceded the coupling of indole derivatives with various alkenyl bromides, such as aromatic and heteroaromatics, alpha- and beta-substituted as well as exo- and endo-cyclic alkenyl compounds. An extensive mechanistic investigation, including controlled study, reactivity experiments, kinetics and labeling studies, and EPR and XPS analyses, highlights that the alkenylation proceeds through a single-electron transfer process comprising an odd-electron oxidative addition of alkenyl bromide. Furthermore, the alkenylation operates via a probable Ni(I)/Ni(III) pathway involving the rate-limiting C-H nickelation of indole.</p>10aalkenylation10aC-H activation10aindoles10aMechanism10aNickel10asingle-electron transfer1 aJagtap, Rahul, A.1 aVinod, C., P.1 aPunji, Benudhar  uhttps://library.ncl.res.in/content/nickel-catalyzed-straightforward-and-regioselective-c-h-alkenylation-indoles-alkenyl