Suzuki–Miyaura Cross??Coupling under Solvent??Free Conditions

AF Asachenko, KR Sorochkina…

Index: Asachenko, Andrey F.; Sorochkina, Kristina R.; Dzhevakov, Pavel B.; Topchiy, Maxim A.; Nechaev, Mikhail S. Advanced Synthesis and Catalysis, 2013 , vol. 355, # 18 p. 3553 - 3557

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Citation Number: 5

Abstract

Abstract: A solvent-free reaction protocol for Suzuki–Miyaura cross-couplings was developed.(Hetero) aryl bromides and chlorides are coupled with pinacol arylboronates in high yields. The reaction is catalyzed by conventional bis (triphenylphosphine) palladium (II) chloride [(PPh3) 2PdCl2] and/or palladium (II) acetate/SPhos[PdACHTUNGTRENNUNG (OAc) 2/SPhos] under air. Keywords: carbenes; palladium; phosphanes; solvent-free ...

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106-38-7

4-Bromotoluene

4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane Structure

195062-57-8

4,4,5,5-Tetrame...

~96%

BI-P-TOLYL Structure

613-33-2

BI-P-TOLYL

4-Chlorotoluene Structure

106-43-4

4-Chlorotoluene

4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane Structure

195062-57-8

4,4,5,5-Tetrame...

~93%

BI-P-TOLYL Structure

613-33-2

BI-P-TOLYL

3-Thienylboronic acid Structure

6165-69-1

3-Thienylboroni...

Pinacol Structure

76-09-5

Pinacol

~92%

thiophene-3-boronic acid pinacol ester Structure

214360-70-0

thiophene-3-bor...

Pinacol Structure

76-09-5

Pinacol

3-Nitrophenylboronic acid Structure

13331-27-6

3-Nitrophenylbo...

~95%

3-Nitrophenylboronic acid pinacol ester Structure

68716-48-3

3-Nitrophenylbo...

4-Bromobenzaldehyde Structure

1122-91-4

4-Bromobenzaldehyde

4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane Structure

195062-57-8

4,4,5,5-Tetrame...

~92%

4'-Methylbiphenyl-4-carbaldehyde Structure

36393-42-7

4'-Methylbiphen...

1-Bromo-2-nitrobenzene Structure

577-19-5

1-Bromo-2-nitro...

4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane Structure

195062-57-8

4,4,5,5-Tetrame...

~91%

4-METHYL-2?-NITROBIPHENYL Structure

70680-21-6

4-METHYL-2?-NIT...

4-Bromotoluene Structure

106-38-7

4-Bromotoluene

~%

4-METHYL-2?-NITROBIPHENYL Structure

70680-21-6

4-METHYL-2?-NIT...

2-Bromoaniline Structure

615-36-1

2-Bromoaniline

4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane Structure

195062-57-8

4,4,5,5-Tetrame...

~78%

2-(4-methylphenyl)aniline Structure

1204-43-9

2-(4-methylphen...

9-Bromoanthracene Structure

1564-64-3

9-Bromoanthracene

4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane Structure

195062-57-8

4,4,5,5-Tetrame...

~10%

Anthracene,9-(4-methylphenyl)- Structure

23674-14-8

Anthracene,9-(4...

4-Bromotoluene Structure

106-38-7

4-Bromotoluene

~%

Anthracene,9-(4-methylphenyl)- Structure

23674-14-8

Anthracene,9-(4...

4-Tolylboronic acid Structure

5720-05-8

4-Tolylboronic acid

~%

Anthracene,9-(4-methylphenyl)- Structure

23674-14-8

Anthracene,9-(4...

Bromobenzene Structure

108-86-1

Bromobenzene

4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane Structure

195062-57-8

4,4,5,5-Tetrame...

~98%

4-Phenyltoluene Structure

644-08-6

4-Phenyltoluene

2-Chlorotoluene Structure

95-49-8

2-Chlorotoluene

4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane Structure

195062-57-8

4,4,5,5-Tetrame...

~90%

24DIMETHYLBIPHENYL Structure

611-61-0

24DIMETHYLBIPHENYL

2-Bromotoluene Structure

95-46-5

2-Bromotoluene

4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane Structure

195062-57-8

4,4,5,5-Tetrame...

~99%

24DIMETHYLBIPHENYL Structure

611-61-0

24DIMETHYLBIPHENYL

4-Tolylboronic acid Structure

5720-05-8

4-Tolylboronic acid

~%

24DIMETHYLBIPHENYL Structure

611-61-0

24DIMETHYLBIPHENYL

3-Bromotoluene Structure

591-17-3

3-Bromotoluene

4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane Structure

195062-57-8

4,4,5,5-Tetrame...

~96%

3,4'-dimethyl-1,1'-biphenyl Structure

7383-90-6

3,4'-dimethyl-1...

2-Bromotoluene Structure

95-46-5

2-Bromotoluene

Isopropoxyboronic acid pinacol ester Structure

61676-62-8

Isopropoxyboron...

~77%

4,4,5,5-Tetramethyl-2-(2-methylphenyl)-1,3,2-dioxaborolane Structure

195062-59-0

4,4,5,5-Tetrame...

3-Bromopyridine Structure

626-55-1

3-Bromopyridine

4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane Structure

195062-57-8

4,4,5,5-Tetrame...

~98%

3-(4-Methylphenyl)pyridine Structure

4423-09-0

3-(4-Methylphen...

3-Chloropyridine Structure

626-60-8

3-Chloropyridine

4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane Structure

195062-57-8

4,4,5,5-Tetrame...

~98%

3-(4-Methylphenyl)pyridine Structure

4423-09-0

3-(4-Methylphen...

4-Tolylboronic acid Structure

5720-05-8

4-Tolylboronic acid

~%

3-(4-Methylphenyl)pyridine Structure

4423-09-0

3-(4-Methylphen...

Pinacol Structure

76-09-5

Pinacol

4-Fluorobenzeneboronic acid Structure

1765-93-1

4-Fluorobenzene...

~91%

2-(4-FLUOROPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE Structure

214360-58-4

2-(4-FLUOROPHEN...

3-Chloro-6-methoxypyridazine Structure

1722-10-7

3-Chloro-6-meth...

4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane Structure

195062-57-8

4,4,5,5-Tetrame...

~59%

3-methoxy-6-(4-methylphenyl)pyridazine Structure

10330-56-0

3-methoxy-6-(4-...

4-Bromotoluene Structure

106-38-7

4-Bromotoluene

~%

3-methoxy-6-(4-methylphenyl)pyridazine Structure

10330-56-0

3-methoxy-6-(4-...

4-Tolylboronic acid Structure

5720-05-8

4-Tolylboronic acid

~%

3-methoxy-6-(4-methylphenyl)pyridazine Structure

10330-56-0

3-methoxy-6-(4-...

2,6-Dichloropyridine Structure

2402-78-0

2,6-Dichloropyridine

4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane Structure

195062-57-8

4,4,5,5-Tetrame...

~63%

2,6-di(4-methylphenyl)pyridine Structure

14435-88-2

2,6-di(4-methyl...

4-Tolylboronic acid Structure

5720-05-8

4-Tolylboronic acid

~%

3,4'-dimethyl-1,1'-biphenyl Structure

7383-90-6

3,4'-dimethyl-1...

Pinacol Structure

76-09-5

Pinacol

3-(Trifluoromethyl)phenylboronic acid Structure

1423-26-3

3-(Trifluoromet...

~93%

4,4,5,5-TETRAMETHYL-2-(3-(TRIFLUOROMETHYL)PHENYL)-1,3,2-DIOXABOROLANE Structure

325142-82-3

4,4,5,5-TETRAME...

QVR CE Structure

585-76-2

QVR CE

4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane Structure

195062-57-8

4,4,5,5-Tetrame...

~76%

4'-Methyl-3-biphenylcarboxylic acid Structure

147404-69-1

4'-Methyl-3-bip...

4-Bromotoluene Structure

106-38-7

4-Bromotoluene

3-Nitrophenylboronic acid pinacol ester Structure

68716-48-3

3-Nitrophenylbo...

~10%

4'-Methyl-3-nitro-1,1'-biphenyl Structure

53812-68-3

4'-Methyl-3-nit...

4-Bromotoluene Structure

106-38-7

4-Bromotoluene

2-(4-FLUOROPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE Structure

214360-58-4

2-(4-FLUOROPHEN...

~90%

4-FLUORO-4'-METHYL-1,1'-BIPHENYL Structure

72093-43-7

4-FLUORO-4'-MET...

1-Bromo-4-fluorobenzene Structure

460-00-4

1-Bromo-4-fluor...

4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane Structure

195062-57-8

4,4,5,5-Tetrame...

~89%

4-FLUORO-4'-METHYL-1,1'-BIPHENYL Structure

72093-43-7

4-FLUORO-4'-MET...

4-Bromotoluene Structure

106-38-7

4-Bromotoluene

~%

4-FLUORO-4'-METHYL-1,1'-BIPHENYL Structure

72093-43-7

4-FLUORO-4'-MET...

4-Tolylboronic acid Structure

5720-05-8

4-Tolylboronic acid

~%

4-FLUORO-4'-METHYL-1,1'-BIPHENYL Structure

72093-43-7

4-FLUORO-4'-MET...

4-Fluorobenzeneboronic acid Structure

1765-93-1

4-Fluorobenzene...

~%

4-FLUORO-4'-METHYL-1,1'-BIPHENYL Structure

72093-43-7

4-FLUORO-4'-MET...

2-Bromochlorobenzene Structure

694-80-4

2-Bromochlorobenzene

4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane Structure

195062-57-8

4,4,5,5-Tetrame...

~98%

4-METHYL-2-CHLOROBIPHENYL Structure

19493-33-5

4-METHYL-2-CHLO...

4-Bromotoluene Structure

106-38-7

4-Bromotoluene

~%

4-METHYL-2-CHLOROBIPHENYL Structure

19493-33-5

4-METHYL-2-CHLO...

4-Tolylboronic acid Structure

5720-05-8

4-Tolylboronic acid

~%

4-METHYL-2-CHLOROBIPHENYL Structure

19493-33-5

4-METHYL-2-CHLO...

bromoanisole Structure

578-57-4

bromoanisole

4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane Structure

195062-57-8

4,4,5,5-Tetrame...

~10%

1-methoxy-2-(4-methylphenyl)benzene Structure

92495-53-9

1-methoxy-2-(4-...

4-Bromotoluene Structure

106-38-7

4-Bromotoluene

~%

1-methoxy-2-(4-methylphenyl)benzene Structure

92495-53-9

1-methoxy-2-(4-...

4-Tolylboronic acid Structure

5720-05-8

4-Tolylboronic acid

~%

1-methoxy-2-(4-methylphenyl)benzene Structure

92495-53-9

1-methoxy-2-(4-...

4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane Structure

195062-57-8

4,4,5,5-Tetrame...

2-Bromobenzoic acid Structure

88-65-3

2-Bromobenzoic acid

~99%

4'-Methyl-[1,1'-biphenyl]-2-carboxylic acid Structure

7148-03-0

4'-Methyl-[1,1'...

1-Bromo-4-nitrobenzene Structure

586-78-7

1-Bromo-4-nitro...

4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane Structure

195062-57-8

4,4,5,5-Tetrame...

~96%

4-METHYL-4'-NITRO-1,1'-BIPHENYL Structure

2143-88-6

4-METHYL-4'-NIT...

4-Chloronitrobenzene Structure

100-00-5

4-Chloronitrobenzene

4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane Structure

195062-57-8

4,4,5,5-Tetrame...

~78%

4-METHYL-4'-NITRO-1,1'-BIPHENYL Structure

2143-88-6

4-METHYL-4'-NIT...

4-Tolylboronic acid Structure

5720-05-8

4-Tolylboronic acid

~%

4-METHYL-4'-NITRO-1,1'-BIPHENYL Structure

2143-88-6

4-METHYL-4'-NIT...

4-Bromobenzoic acid Structure

586-76-5

4-Bromobenzoic acid

4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane Structure

195062-57-8

4,4,5,5-Tetrame...

~97%

4'-Methyl-4-biphenylcarboxylic acid Structure

720-73-0

4'-Methyl-4-bip...

3-Bromobenzaldehyde Structure

3132-99-8

3-Bromobenzaldehyde

4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane Structure

195062-57-8

4,4,5,5-Tetrame...

~10%

4'-Methyl-[1,1'-biphenyl]-3-carbaldehyde Structure

116470-54-3

4'-Methyl-[1,1'...

2-Chlorobenzaldehyde Structure

89-98-5

2-Chlorobenzaldehyde

4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane Structure

195062-57-8

4,4,5,5-Tetrame...

~92%

4'-METHYL-[1,1'-BIPHENYL]-2-CARBALDEHYDE Structure

16191-28-9

4'-METHYL-[1,1'...

2-Chloropyridine Structure

109-09-1

2-Chloropyridine

4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane Structure

195062-57-8

4,4,5,5-Tetrame...

~45%

2-p-tolylpyridine Structure

4467-06-5

2-p-tolylpyridine

2-Bromopyridine Structure

109-04-6

2-Bromopyridine

4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane Structure

195062-57-8

4,4,5,5-Tetrame...

~74%

2-p-tolylpyridine Structure

4467-06-5

2-p-tolylpyridine


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