Synthesis of 9-alkylidene-9H-fluorenes by a novel palladium-catalyzed rearrangement

Authors
Tian, QP Larock, RC
Citation
Qp. Tian et Rc. Larock, Synthesis of 9-alkylidene-9H-fluorenes by a novel palladium-catalyzed rearrangement, ORG LETT, 2(21), 2000, pp. 3329-3332
Citations number
16
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
21
Year of publication
2000
Pages
3329 - 3332
Database
ISI
SICI code
1523-7060(20001019)2:21<3329:SO9BAN>2.0.ZU;2-I
Abstract
[GRAPHICS] In the presence of a palladium catalyst and NaOAc, aryl iodides react with 1-aryl-1-alkynes to afford 9-alkylidene-9H-fluorenes in good yields. This p rocess appears to involve (1) oxidative addition of the aryl iodide to Pd(0 ), (2) alkyne insertion, (3) rearrangement of the resulting vinylic palladi um intermediate to an arylpalladium species, and (4) aryl-aryl coupling wit h simultaneous regeneration of the Pd(0) catalyst.