scholarly journals Iodobenzene-catalyzed synthesis of aryl sulfonate esters from aminoquinolines via remote radical C–O cross-coupling

RSC Advances ◽  
2017 ◽  
Vol 7 (78) ◽  
pp. 49436-49439 ◽  
Author(s):  
Chao Shen ◽  
Ming Yang ◽  
Jun Xu ◽  
Chao Chen ◽  
Kai Zheng ◽  
...  
Keyword(s):  
Transition Metal ◽  
Cross Coupling ◽  
Metal Catalysts ◽  
Transition Metal Catalysts ◽  
Efficient Approach

A simple and efficient approach is established for the iodobenzene-catalyzed synthesis of aryl sulfonate esters from aminoquinolines via remote radical C–O cross-coupling in the absence of any transition metal catalysts.

Synthesis of spiroketals by iridium-catalyzed double hydroalkoxylation

2006 ◽  
Vol 78 (2) ◽  
pp. 385-390 ◽  
Author(s):  
Barbara A. Messerle ◽  
Khuong Q. Vuong
Keyword(s):  
Transition Metal ◽  
Benzyl Alcohol ◽  
Metal Catalysts ◽  
Transition Metal Catalysts ◽  
Iridium Complex ◽  
Effective Catalyst ◽  
Efficient Approach ◽  
Highly Efficient

A highly efficient approach to the synthesis of spiroketals involves the double cyclization of alkynyl diols using transition-metal catalysts. The iridium complex [Ir(PyP)(CO)2]BPh4 where PyP = 1-[(2-diphenylphosphino)ethyl]pyrazole is an effective catalyst for promoting the formation of spiroketals via this double hydroalkoxylation reaction. The complex promotes the formation of a series of spiroketal products from alkynyl diol starting materials such as 3-ethynylpentane-1,5-diol and 2-(4-hydroxybut-1-ynyl)benzyl alcohol. Stereoselective cyclization occurs for 3-ethynylpentane-1,5-diol, 3-ethynylhexane-1,6-diol. The cycloadditions occur in all but one case with quantitative conversion in under 24 h at 120 °C.

Transition-metal-free direct perfluoroalkylation of quinoline amides at C5 position through radical cross-coupling under mild conditions

2017 ◽  
Vol 4 (6) ◽  
pp. 1116-1120 ◽  
Author(s):  
Jun Xu ◽  
Li Qiao ◽  
Beibei Ying ◽  
Xiaolei Zhu ◽  
Chao Shen ◽  
...  
Keyword(s):  
Transition Metal ◽  
Efficient Method ◽  
Cross Coupling ◽  
Metal Catalysts ◽  
Transition Metal Catalysts ◽  
Low Energy ◽  
Metal Free ◽  
Mild Conditions

A simple low-energy and efficient method is established for the synthesis of C5-selective perfluoroalkylation quinolines in the absence of any transition metal catalysts.

Recent Advances in Cross-Couplings of Functionalized Organozinc Reagents

Synthesis ◽  
2021 ◽  
Author(s):  
Baosheng Wei ◽  
Paul Knochel
Keyword(s):  
Transition Metal ◽  
Room Temperature ◽  
Cross Coupling ◽  
Metal Catalysts ◽  
Transition Metal Catalysts ◽  
Iron Catalysts ◽  
Organic Azides ◽  
Recent Advances ◽  
Organozinc Reagents

Cross-couplings involving organozinc reagents require usually a Pd-catalysis (Negishi cross-coupling), however, uncatalyzed cross-couplings of zinc organometallics proceed well in the absence of transition-metal catalysts with reactive electrophiles such as benzal 1,1-diacetates, benzhydryl acetates, and iminium trifluoroacetates. Also, organozinc compounds undergo C-N bond formations with O-benzoylhydroxylamines or organic azides in the presence of cobalt- or iron-catalysts. Besides, highly diastereoselective and enantioselective cross-couplings can be readily performed with room-temperature configurationally stable alkylzinc species producing diastereoselectively and enantiomerically enriched products. Finally, highly regioselective magnesiations of functionalized arenes and heteroarenes undergo Negishi (after transmetalation with ZnCl2) or Cu-catalyzed cross-couplings. 1 Introduction 2 Uncatalyzed Cross-Couplings of Organozinc Reagents with Highly Electrophilic Partners 3 Iron- and Cobalt-catalyzed Aminations Using Organozinc Reagents 4 Stereo- and Regioselective Cross-couplings of Organozinc Reagents 5 Conclusion

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