PdCl₂-Catalyzed Reduction of Organic Halides by Triethylsilane

Abstract

The palladium-catalyzed dehalogenation reaction of alkyl or aryl halides with triethylsilane takes place, giving high yields under mild reaction conditions. The efficiency of the reduction is similar for organic chlorides, bromides, or iodides, and the presence of functionalities such as esters or ethers does not interfere with the outcome of the reaction.

Integrated Palladium‐Catalyzed Arylation of Heavier Group 14 Hydrides

“…[12] Although, satisfactory results were obtained for the preparation of aryltrialkoxysilanes, arylation of trialkylsilane [13] has met with limited success due to the tendency to give a reduced product (Scheme 1a). [14,15] Attention has also been paid to the Pd-catalyzed arylation of trisA C H T U N G T R E N N U N G (2-furyl)germane [16] or hydrogermatrane [8e] with aryl halides. Despite these significant advances, other examples of arylation of hydrogermanes with aryl halides have not been described to date.…”

Pd/C‐Catalyzed Transfer Reduction of Aryl Chlorides with Sodium Formate in Water

“…Therefore, the aid of a stable hydrogen donor represents a useful alternative method to the catalytic hydrodechlorination of aromatic chlorides by molecular hydrogen. These dechlorination systems involve the use of metal hydrides, [17] metal alkoxides, [6,18] hydrosilanes, [19,20] Grignard reagents, [21] alcohols, [22] and formic acid and its salts [23,24] as the hydrogen source. Formic acid and its salts are particularly versatile, and cheap reagents that have been used as a source of hydrogen in catalytic transfer hydrogenations and have frequently been applied in the reduction of a large variety of functional groups.…”

A mild and efficient palladium–triethylsilane system for reduction of olefins and carbon–carbon double bond isomerization

“…First, during the dehalogenation reaction of alkyl or aryl halides [equation (1)], we have identified using GC/MS the presence of small amounts of Et 3 SiCl along the corresponding silyl halide, independently of the starting halide. 32 The presence of Et 3 SiCl may account for a complex process (oxidative addition followed by a reductive elimination) during the reaction. It is believed that the active catalyst species during the reaction is the Pd(0) generated in situ according to equation (2).…”

“…It was successfully applied for the conversion of organic halides to the corresponding alkanes 32 and for the conversion of alcohols to their corresponding halides and alkanes. 33 The versatility of the system Et 3 SiH-PdCl 2 was also demonstrated for the reduction of olefins to alkanes, 34 conversion of alcohols to their corresponding silyl ethers and cleavage of the triethylsilyl ethers to the parent alcohols, 35 and for the efficient isomerization of 1-alkenes to 2-and 3-alkenes.…”