ChemInform Abstract: σ-Complexes of Transition Metals in Organic Synthesis. Part 1. Cross- Coupling Reactions of Organo-Titanium Compounds with Allylic Halides in the Presence of Palladium Complexes.

ChemInform ◽  
1987 ◽  
Vol 18 (36) ◽  
Author(s):  
A. N. KASATKIN ◽  
A. N. KULAK ◽  
G. A. TOLSTIKOV
Keyword(s):  
Transition Metals ◽  
Organic Synthesis ◽  
Cross Coupling ◽  
Palladium Complexes ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Complexes Of Transition Metals ◽  
Titanium Compounds ◽  
Allylic Halides

scholarly journals Iron-Catalyzed C–H Functionalizations under Triazole-Assistance

Molecules ◽  
2020 ◽  
Vol 25 (8) ◽  
pp. 1806 ◽  
Author(s):  
Matteo Lanzi ◽  
Gianpiero Cera
Keyword(s):  
Transition Metals ◽  
Organic Synthesis ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
Efficient Catalyst ◽  
Widespread Application ◽  
Promising Alternative ◽  
Cross Coupling Reactions ◽  
Benign Nature

3d transition metals-catalyzed C–H bond functionalizations represent nowadays an important tool in organic synthesis, appearing as the most promising alternative to cross-coupling reactions. Among 3d transition metals, iron found widespread application due to its availability and benign nature, and it was established as an efficient catalyst in organic synthesis. In this context, the use of ortho-orientating directing groups (DGs) turned out to be necessary for promoting selective iron-catalyzed C–H functionalization reactions. Very recently, triazoles DGs were demonstrated to be more than an excellent alternative to the commonly employed 8-aminoquinoline (AQ) DG, as a result of their modular synthesis as well as the mild reaction conditions applied for their removal. In addition, their tunable geometry and electronics allowed for new unprecedented reactivities in iron-catalyzed C–H activation methodologies that will be summarized within this review.

scholarly journals Capturing the Most Active State of a Palladium(0) Cross-Coupling Catalyst

2021 ◽  
Author(s):  
Sii Hong Lau ◽  
Liye Chen ◽  
Illia Kevlishvili ◽  
Katherine Davis ◽  
Peng Liu ◽  
...  
Keyword(s):  
Organic Synthesis ◽  
Cryogenic Temperature ◽  
Active Form ◽  
Cross Coupling ◽  
Active Species ◽  
Palladium Complexes ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Solid State Characterization

Zerovalent palladium complexes are ubiquitous active species in modern cross-coupling reactions that comprise many premier methods for the construction of C–C and C–heteroatom bonds in organic synthesis. While palladium(0) complexes stabilized by two or more dative ligands are widely known, the most active form of Pd(0) coordinated by a single ancillary ligand (“monoligated Pd(0)”) has long eluded direct characterization. We report the synthesis and unambiguous solution- and solid-state characterization of functionally 12-electron Pd(0) complexes coordinated by a single tri(1-adamantyl)phosphine (PAd3) ligand. Access to these fleeting intermediates was achieved by enabling B-to-Pd transmetalation reactions that occur at cryogenic temperature. This work opens new avenues to experimentally interrogate highly reactive on-cycle Pd(0) catalysts and their structure-dependent reactivity and speciation, which should be broadly informative in continuing studies of catalytic processes featuring the prevalent Pd(0)/Pd(II) redox couple.

Cross-Coupling Reactions with 2-Amino-/Acetylamino-Substituted 3-Iodo-1,4-naphthoquinones: Convenient Synthesis of Novel Alkenyl- and Alkynylnaphthoquinones and Derivatives

Synthesis ◽  
2021 ◽  
Author(s):  
Felipe C. Demidoff ◽  
Leandro L. de Carvalho ◽  
Eduardo José P. Rodrigues Filho ◽  
Andréa Luzia F. de Souza ◽  
Chaquip D. Netto
Keyword(s):  
Click Chemistry ◽  
Organic Synthesis ◽  
Biological Activities ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Large Array ◽  
Terminal Alkyne ◽  
Co Catalyst ◽  
Cross Coupling Reactions ◽  
Convenient Synthesis

AbstractFunctionalized 1,4-naphthoquinones have been employed as versatile synthons in organic synthesis, in addition to presenting a large array of biological activities. Herein, the applications of 2-amino-/ acetylamino-substituted 3-iodo-1,4-naphthoquinones in cross-coupling reactions are described to successfully afford sixteen novel 3-styryl-1,4-naphthoquinones (amino-stilbene-quinone hybrids) and four 3-alkynyl-1,4-naphthoquinone in overall good yields. Interestingly, the alkynylated derivatives could be obtained from ligand- and Pd-free CuI-mediated cross-coupling reactions, after extensive investigations to exclude Pd as a co-catalyst. Lastly, the desilanized terminal alkyne was subjected to click chemistry reactions to give two novel triazole-1,4-naphthoquinone hybrids.

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