Synthesis of alkyl- and aryldiphenylphosphines via electrogenerated magnesium chloride diphenylphosphanide

Nechab, Malek; Gall, Erwan Le; Troupel, Michel; Nédélec, Jean‐Yves

doi:10.1016/j.jorganchem.2006.01.001

Cited by 5 publications

(2 citation statements)

References 16 publications

(16 reference statements)

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“…The solvent was removed and the product was purified by column chromatography (ethyl acetate–hexane, 10:90; 0.64 g; 0.22 mmol; 81%). This compound has been previously reported in the literature 7…”

Section: Methodsmentioning

confidence: 67%

Palladium‐catalysed PC bond forming reactions between diphenylphosphine and ortho‐substituted aryl bromides

Damian

Clarke

Cobley

2009

Applied Organom Chemis

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The use of palladium catalysts derived from 1,1 -bis-diisopropylphosphino-ferrocene and a microwave heating source allows the coupling of a range of ortho-substituted aryl bromides to diphenylphosphine derivatives to proceed in good yield in under 30 min. Optimization studies reveal that the combination of diphenylphosphine and DABCO is superior to more basic phosphide nucleophiles such as Ph 2 PK or Ph 2 PMgBr. High yields are only observed when moderately bulky electron rich diphosphines are used as ligands. The differences between P-C coupling and other cross-coupling reactions are discussed in the light of the reactivity observed. Studies aimed at producing industrially important 1,2-bis-phosphino-benzene ligands are also described.

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Section: Methodsmentioning

confidence: 67%

Palladium‐catalysed PC bond forming reactions between diphenylphosphine and ortho‐substituted aryl bromides

Damian

Clarke

Cobley

2009

Applied Organom Chemis

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“…Occasionally, other organophosphorus substrates are used in these reactions; Scheme 41 shows how Ph 2 PCl was converted electrochemically to Ph 2 PMgCl, which was cross-coupled with aryl bromides using the catalyst precursor NiBr 2 (bipy) [66].…”

Section: Pd-and Ni-catalyzed Reactionsmentioning

confidence: 99%

Recent Advances in Metal-Catalyzed C–P Bond Formation

Glueck

2010

C-X Bond Formation

159

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This chapter describes recent advances in metal-catalyzed C-P bond formation, which may be classified into two types of reactions. In hydrophosphination and related processes, P-H groups add across unsaturated C-X (X ¼ C, N, O) bonds. Phosphination of electrophiles typically results in substitution at sp 2 or sp 3 carbon; the P-H group is removed, often by a base. The scope of both nucleophilic and electrophilic partners in these processes is surveyed, and the proposed mechanisms and intermediates in the metal-catalyzed reactions are described.

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Benzyl Diphenylphosphine

Karp

2021

Encyclopedia of Reagents for Organic Synthesis

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Synthesis of alkyl- and aryldiphenylphosphines via electrogenerated magnesium chloride diphenylphosphanide

Cited by 5 publications

References 16 publications

Palladium‐catalysed PC bond forming reactions between diphenylphosphine and ortho‐substituted aryl bromides

Palladium‐catalysed PC bond forming reactions between diphenylphosphine and ortho‐substituted aryl bromides

Recent Advances in Metal-Catalyzed C–P Bond Formation

Benzyl Diphenylphosphine

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