Palladium-Catalyzed Cross-Coupling Reactions of Allyl, Phenyl, Alkenyl, and Alkynyl Germatranes with Aryl Iodides

Abstract

The potential of using organogermatranes in palladium-catalyzed cross-coupling with aryl iodides has been investigated. We have found that organogermatranes are less reactive in this analogue of Stille coupling than trialkylorganostannanes; nevertheless activation by fluoride promotes the reaction. The hypervalent germanium species produced from the germatranes provide a more efficient and more easily handled reagent than trialkoxygermanium analogues.

Palladium‐Catalyzed Cross‐Coupling Reaction Using Arylgermanium Sesquioxide

“…Recently, Faller et al developed an analogous reagent, arylgermatrane. [5] Oshima and co-workers reported that organotriA C H T U N G T R E N N U N G (2-furyl)germanes act as efficient coupling reagents. [6] Although the former reagent is easy to prepare, it is not only highly toxic, but also not so high yielding.…”

Cross‐Coupling Reactions to sp Carbon Atoms

“…Compound 140 did indeed give a moderate yield of the cross-coupled product, with 4-bromotoluene catalyzed by [Pd 2 (dba) 3 ] and PPh(o-Tol) 2 , although elevated temperatures were required (Table 9.25). Following this concept, alkynylgermatranes 141 were reported that were able to undergo cross-coupling with iodoarenes on activation with TBAF [365]. The alkynylgermatranes 141 were readily prepared from the corresponding alkynylgermanium trichlorides.…”

Transition Metal Catalyzed CarbonCarbon Bond Formation: The Key of Homogeneous Catalysis

“…IV): the Suzuki-Miyaura reaction (Y ¼ B) [8][9][10][11]; the Migita-Kosugi-Stille reaction (Y ¼ Sn) [12][13][14][15]; the Sonogashira coupling reaction (Y ¼ Cu) [7,16,17]; the Kumada-Tamao-Corriu reaction (Y ¼ Mg) [18][19][20]; the Hiyama reaction (Y ¼ Si) [21][22][23][24]; and the Negishi coupling (Y ¼ Zn) [25][26][27]. Other organometallic and heteroatom species, Y ¼ Al, Ge, In, Ag, Te, S, have been also tested as reagents for the transmetallation step [28][29][30][31][32][33][34][35].…”