957055-41-3Relevant articles and documents
Indole-derived arynes and their diels - Alder reactivity with furans
Buszek, Keith R.,Luo, Diheng,Kondrashov, Mikhail,Brown, Neil,VanderVelde, David
, p. 4135 - 4137 (2008/02/13)
Arynes derived from any position of the ubiquitous indole nucleus are unknown. We have now provided the first evidence for the formation and trapping of the 4,5-, 5,6-, and 6,7-indolynes. A series of o-dihalo indoles (CI, Br, F) were synthesized and reacted under metal-halogen exchange conditions to give Diels-Alder cycloadducts in high yield with furan. The use of an excess of fert-butyllithium resulted in the rearrangement of the initially formed cycloadduct; however, employing only a slight excess of n-butyllithium cleanly gave cycloadducts with furan.