1,3,5-Tris[(2-hydroxy-3,5-diphenyl)phenyl]benzene and its Phenoxyl Radicals

Deckert‐Gaudig, Tanja; Hünig, Siegfried; Dormann, E.; Kelemen, M.T.

doi:10.1002/1099-0690(200104)2001:8<1563::aid-ejoc1563>3.0.co;2-s

Cited by 3 publications

(1 citation statement)

References 44 publications

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“…3‐Bomo‐4‐methoxybiphenyl (8na): 75 Following the general procedure, 8na obtained from 1n (366 mg, 1.5 mmol) and 7a (276 mg, 1.5 mmol) as a colourless solid; yield: 128 mg (32%), mp 80 °C; along with 9a [yield: 53 mg (23%)]. 1 H NMR (300 MHz, CDCl 3 ): δ =7.80 (d, J =2.2 Hz, 1 H), 7.59–7.47 (3 H), 7.43 (m, 2 H), 7.33 (m, 1 H), 6.97 (d, J =8.5 Hz, 1 H), 3.94 (s, 3 H); 13 C NMR (75 MHz, CDCl 3 ): δ =155.4 (0), 139.5 (0), 135.3 (0), 132.0 (1), 128.9 (1), 127.3 (1), 127.1 (1), 126.8 (1), 112.2 (1), 112.1 (0), 56.4 (3); MS (EI): m / z =139 (48%), 219 (25%), 247 (43%), 262 ([M] + , 100%); HR‐MS (EI): m / z =261.9978, calcd.…”

Section: Methodsmentioning

confidence: 99%

A Deacetylation–Diazotation–Coupling Sequence: Palladium‐ Catalyzed CC Bond Formation with Acetanilides as Formal Leaving Groups

Schmidt¹,

Berger²

2013

Adv Synth Catal

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Acetanilides can be deacetylated and diazotized in situ, and subsequently used in Pd-catalyzed coupling reactions without isolation of the diazonium intermediate. Heck reactions, Suzuki crosscoupling reactions, and a Pd-catalyzed [2 + 2 + 1] cycloaddition have been investigated as terminating C À C bond-forming steps of this one-flask sequence. The sequence does not require the exchange of solvents or removal of by-products between the individual steps, but proceeds by addition of reagents and catalysts in due course.

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Section: Methodsmentioning

confidence: 99%

A Deacetylation–Diazotation–Coupling Sequence: Palladium‐ Catalyzed CC Bond Formation with Acetanilides as Formal Leaving Groups

Schmidt¹,

Berger²

2013

Adv Synth Catal

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11.2 Carbocycles (2/4)

Mecke

Jäger

Nitrogen and Oxygen Centered Radicals

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Gold-Catalyzed Direct Arylation

Ball

Lloyd‐Jones

Russell

2012

Science

384

175

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Biaryls (two directly connected aromatic rings, Ar(1)-Ar(2)) are common motifs in pharmaceuticals, agrochemicals, and organic materials. Current methods for establishing the Ar(1)-Ar(2) bond are dominated by the cross-coupling of aryl halides (Ar(1)-X) with aryl metallics (Ar(2)-M). We report that, in the presence of 1 to 2 mole percent of a gold catalyst and a mild oxidant, a wide range of arenes (Ar(1)-H) undergo site-selective arylation by arylsilanes (Ar(2)-SiMe(3)) to generate biaryls (Ar(1)-Ar(2)), with little or no homocoupling (Ar(1)-Ar(1)/Ar(2)-Ar(2)). Catalysis proceeds at room temperature and tolerates a broad range of functional groups, including those incompatible with cross-coupling. These features expedite biaryl preparation, as demonstrated by synthesis of the nonsteroidal anti-inflammatory diflunisal.

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1,3,5-Tris[(2-hydroxy-3,5-diphenyl)phenyl]benzene and its Phenoxyl Radicals

Cited by 3 publications

References 44 publications

A Deacetylation–Diazotation–Coupling Sequence: Palladium‐ Catalyzed CC Bond Formation with Acetanilides as Formal Leaving Groups

A Deacetylation–Diazotation–Coupling Sequence: Palladium‐ Catalyzed CC Bond Formation with Acetanilides as Formal Leaving Groups

11.2 Carbocycles (2/4)

Gold-Catalyzed Direct Arylation

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