title: Indole-derived arynes and their Diels-Alder reactivity with furans.
abstract: 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 (Cl, 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 tert-butyllithium resulted in the rearrangement of the initially formed cycloadduct; however, employing only a slight excess of n-butyllithium cleanly gave cycloadducts with furan.
authors: Department of Chemistry, Kansas State University, 111 Willard Hall, Manhattan, Kansas 66506, USA. buszekk@umkc.edu
authors: Keith R
authors: KR
authors: Buszek
authors: Diheng
authors: D
authors: Luo
authors: Mikhail
authors: M
authors: Kondrashov
authors: Neil
authors: N
authors: Brown
authors: David
authors: D
authors: VanderVelde
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001555:Benzene Derivatives / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D006574:Heterocyclic Compounds, 2-Ring / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D001555:Benzene Derivatives; D005663:Furans; D006574:Heterocyclic Compounds, 2-Ring; D007211:Indoles; C524146:benzyne