249. The preparation of unsymmetrical diphenyl derivatives

The "ligandless" palladium acetate-catalyzed Suzuki cross-coupling reaction of ArX with aryl- and vinylboronic acids in water without organic cosolvent in the presence of tetrabutylammonium bromide is reported. Aryl bromides give high yields and considerably accelerate the coupling. A wide variety of functional groups can be tolerated. Aryl iodides, however, give incomplete conversion and aryl triflate coupling shows no improvement over reported conditions.

show abstract

“…4-Methoxy-1,1‘-biphenyl (Table , entry 6). Obtained as a white solid, mp 88−90 °C (lit . mp 89−90 °C).…”

Section: Methodsmentioning

confidence: 99%

Highly Efficient Palladium-Catalyzed Boronic Acid Coupling Reactions in Water: Scope and Limitations

et al. 1997

View full text Add to dashboard Cite

show abstract

“…222-230°, whose melting point was (9) G. W. Wheland, This Journal, 64, 900 (1942). (23) °Da ta from Dannley and Zaremsky .10b 1 Results in parentheses are assumed to be of somewhat lower accuracy. Synthesis of Alkylbiphenyls.-4-Methyl-, 3 butyl-and 4-¿-butylbiphenyl were synthesized by decomposing the corresponding nitrosoacetanilides in benzene.…”

Section: Resultsmentioning

confidence: 99%

“…2-Methylbiphenyl was prepared by the method of Sherwood, Short and Stansfield. 23 Its physical properties, as well as those of the other alkylbiphenyls employed in this work, are given in Table IV.…”

Section: Methodsmentioning

confidence: 99%

Arylation of Unsaturated Systems by Free Radicals. I. Arylation of Alkylbenzenes

Rondestvedt¹,

Blanchard²

1955

J. Am. Chem. Soc.

View full text Add to dashboard Cite

The Preparation of Unsymmetrical Biaryls by the Diazo Reaction and the Nitrosoacetylamine Reaction

Bachmann

Hoffman

2011

Organic Reactions

View full text Add to dashboard Cite

The amino group of aromatic amines can be replaced by aryl groups with the formation of unsymmetrical biaryl by two general procedures: (1) by reaction of the aryldiazo hydroxide or acetate with aromatic compounds and (2) by reaction of the nitrosoacetylamine with aromatic compounds, In general the aromatic compounds must be a liquid for no solvent has been found which will not be attacked by the reactive intermediates which are formed in these reactions. Diazo and nirosoacetykeamine reactions are discussed.

show abstract

249. The preparation of unsymmetrical diphenyl derivatives

Cited by 14 publications

References 0 publications

Highly Efficient Palladium-Catalyzed Boronic Acid Coupling Reactions in Water: Scope and Limitations

Highly Efficient Palladium-Catalyzed Boronic Acid Coupling Reactions in Water: Scope and Limitations

Arylation of Unsaturated Systems by Free Radicals. I. Arylation of Alkylbenzenes

The Preparation of Unsymmetrical Biaryls by the Diazo Reaction and the Nitrosoacetylamine Reaction

Contact Info

Product

Resources

About