Arylchlorogermanes/TBAF/"moist" toluene: a promising combination for Pd-catalyzed Germyl-Stille cross-coupling.
نویسندگان
چکیده
The trichlorophenyl,- dichlorodiphenyl,- and chlorotriphenylgermanes undergo Pd-catalyzed cross-couplings with aryl bromides and iodides in the presence of TBAF in toluene with addition of the measured amount of water. One chloride ligand on the Ge center allows efficient activation by fluoride to promote transfer of one, two, or three phenyl groups from the organogermane precursors.
منابع مشابه
Stereocontrolled Formation of Styrenes by Pd(0)-catalyzed Cross-coupling of Photoactivated (E)-Alkenylgermanes with Aryl Bromides
The stereocontrolled synthesis of (E)-configured styrenes via Pd(0)-catalyzed cross-couping of (E)-alkenylgermanes with aryl bromides is described. The germanes employed have bis(naphthalen-2-ylmethyl) substitution to allow photooxidative activation toward coupling and a C8F17-fluorous tag to facilitate purification by fluorous solid-phase extraction (F-SPE). The selectivities obtained suggest ...
متن کاملHeterogeneous Stille and Sonogashira cross-coupling reactions over palladium anchored mesoporous silica catalyst
A Pd-based heterogeneous catalyst (Pd(II)-MCM-41) derived from post-synthesis modification of mesoporous silica, MCM-41, has been successfully employed in catalytic Stille and Sonogashira cross-coupling reactions. The catalyst affords good yields in all cross-coupling reactions. Notably, the catalyst is capable of activating less reactive chlorobenzene with moderate yield in both the coupling r...
متن کاملPalladium-Catalyzed Direct Arylation of 5-Halouracils and 5-Halouracil Nucleosides with Arenes and Heteroarenes Promoted by TBAF
The 1-N-benzyl-5-iodo(or bromo)uracil undergoes Pd-catalyzed [Pd2(dba)3] direct arylation with benzene and other simple arenes in the presence of TBAF in DMF without the necessity of adding any ligands or additives to give 5-arylated uracil analogues. The TBAF-promoted coupling also occurs efficiently with electron rich heteroarenes at 100 °C (1 h) even with only small excess of heteroarenes. T...
متن کاملConstruction of the carbon-chalcogen (S, Se, Te) bond at the 2,6-positions of BODIPY via Stille cross-coupling reaction.
Seven new 2-chalcogen- or 2,6-dichalcogen- (S, Se, Te) BODIPY derivatives were synthesized in good to excellent yields (55-95%) by a Pd-catalyzed C-heteroatom Stille cross-coupling reaction, overcoming the limitations of SNAr. The fluorophores show interesting tunable optical properties associated with the formation of a twisted intramolecular charge transfer excited state and competing intersy...
متن کاملA facile and convenient sequential homobimetallic catalytic approach towards β-methylstyrenes. A one-pot Stille cross-coupling/isomerization strategy.
An efficient one-pot synthetic approach towards β-methylstyrenes is reported. The transformation, based on sequential homobimetallic catalysis, involves a Stille cross-coupling reaction between aryl halides and allyltributylstannane, followed by an in situ palladium-catalyzed conjugative isomerization. The reaction was optimized, and the best results were obtained with 10 mol% Pd(PPh3)2Cl2, 8.0...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Organic letters
دوره 12 4 شماره
صفحات -
تاریخ انتشار 2010