Trapping reactions with highly unstable hydrides of antimony and bismuth

2022 ◽  
Author(s):  
Selina Schneider ◽  
Carsten von Hänisch
Keyword(s):  
Trapping Reactions

(Dipp2NacNac)Ga (Dipp2NacNac = HC{C(Me)N(Dipp)}2; Dipp = 2,6-iPr2C6H3) was used as a trapping reagent for the unstable compounds tBuSbH2 and MeBiH2 to yield (Dipp2NacNac)GaH(SbHtBu) (1) and {(Dipp2NacNac)GaH(BiMe)}2 (2). Moreover, its reactions...

Catch It If You Can: Copper-Catalyzed (Transfer) Hydrogenation Reactions and Coupling Reactions by Intercepting Reactive Intermediates Thereof

Synthesis ◽  
2020 ◽  
Vol 52 (17) ◽  
pp. 2483-2496
Author(s):  
Johannes F. Teichert ◽  
Lea T. Brechmann
Keyword(s):  
Coupling Reaction ◽  
Reactive Intermediates ◽  
Transfer Hydrogenation ◽  
Coupling Reactions ◽  
Bond Forming ◽  
Starting Point ◽  
Bond Forming Reactions ◽  
Hydrogenation Reactions ◽  
Multicomponent Coupling Reactions ◽  
Trapping Reactions

The key reactive intermediate of copper(I)-catalyzed alkyne semihydrogenations is a vinylcopper(I) complex. This intermediate can be exploited as a starting point for a variety of trapping reactions. In this manner, an alkyne semihydrogenation can be turned into a dihydrogen­-mediated coupling reaction. Therefore, the development of copper-catalyzed (transfer) hydrogenation reactions is closely intertwined with the corresponding reductive trapping reactions. This short review highlights and conceptualizes the results in this area so far, with H2-mediated carbon–carbon and carbon–heteroatom bond-forming reactions emerging under both a transfer hydrogenation setting as well as with the direct use of H2. In all cases, highly selective catalysts are required that give rise to atom-economic multicomponent coupling reactions with rapidly rising molecular complexity. The coupling reactions are put into perspective by presenting the corresponding (transfer) hydrogenation processes first.1 Introduction: H2-Mediated C–C Bond-Forming Reactions2 Accessing Copper(I) Hydride Complexes as Key Reagents for Coupling Reactions; Requirements for Successful Trapping Reactions 3 Homogeneous Copper-Catalyzed Transfer Hydrogenations4 Trapping of Reactive Intermediates of Alkyne Transfer Semi­hydrogenation Reactions: First Steps Towards Hydrogenative Alkyne Functionalizations 5 Copper(I)-Catalyzed Alkyne Semihydrogenations6 Copper(I)-Catalyzed H2-Mediated Alkyne Functionalizations; Trapping of Reactive Intermediates from Catalytic Hydrogenations6.1 A Detour: Copper(I)-Catalyzed Allylic Reductions, Catalytic Generation of Hydride Nucleophiles from H2 6.2 Trapping with Allylic Electrophiles: A Copper(I)-Catalyzed Hydro­allylation Reaction of Alkynes 6.3 Trapping with Aryl Iodides7 Conclusion

1,3-Diyl trapping reactions. Fundamental investigations with application to the synthesis of linearly fused tricyclopentanoids

Tetrahedron ◽  
1981 ◽  
Vol 37 (25) ◽  
pp. 4371-4383 ◽  
Author(s):  
R.Daniel Little ◽  
George W. Muller ◽  
Manuel G. Venegas ◽  
Gary L. Carroll ◽  
Ahmed Bukhari ◽  
...  
Keyword(s):  
Trapping Reactions

scholarly journals Solving the puzzling competition of the thermal C2–C6 vs Myers–Saito cyclization of enyne-carbodiimides

2016 ◽  
Vol 12 ◽  
pp. 43-49 ◽  
Author(s):  
Anup Rana ◽  
Mehmet Emin Cinar ◽  
Debabrata Samanta ◽  
Michael Schmittel
Keyword(s):  
Hydrogen Transfer ◽  
Dft Method ◽  
Thermal Cyclization ◽  
Trapping Reactions

The mechanism of the thermal cyclization of enyne-carbodiimides 7a–c has been studied computationally by applying the DFT method. The results indicate that enyne-carbodiimides preferentially follow the C2–C6 (Schmittel) cyclization pathway in a concerted fashion although the Myers–Saito diradical formation is kinetically preferred. The experimentally verified preference of the C2–C6 over the Myers–Saito pathway is guided by the inability of the Myers–Saito diradical to kinetically compete in the rate-determining trapping reactions, either inter- or intramolecular, with the concerted C2–C6 cyclization. As demonstrated with enyne-carbodiimide 11, the Myers–Saito channel can be made the preferred pathway if the trapping reaction by hydrogen transfer is no more rate determining.

Chiral 2-Cyanocinnamates in Conjugate Addition Asymmetric Enolate Trapping Reactions

1992 ◽  
Vol 65 (6) ◽  
pp. 1657-1661 ◽  
Author(s):  
Carlos Cativiela ◽  
Maria Dolores Diaz-De-Villegas ◽  
José Antonio Galvez
Keyword(s):  
Conjugate Addition ◽  
Trapping Reactions

scholarly journals The Phenol–Ene Reaction: Biaryl Synthesis via Trapping Reactions between HDDA-Generated Benzynes and Phenolics

2016 ◽  
Vol 18 (21) ◽  
pp. 5596-5599 ◽  
Author(s):  
Juntian Zhang ◽  
Dawen Niu ◽  
Vincent A. Brinker ◽  
Thomas R. Hoye
Keyword(s):  
Ene Reaction ◽  
Biaryl Synthesis ◽  
Trapping Reactions
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