e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Practical Iron??Catalyzed Allylations of Aryl Grignard Reagents

…, WM Czaplik, A Jacobi von Wangelin

Index: Mayer, Matthias; Czaplik, Waldemar M.; Von Wangelin, Axel Jacobi Advanced Synthesis and Catalysis, 2010 , vol. 352, # 13 p. 2147 - 2152

Full Text: HTML

Citation Number: 59

Abstract

Abstract An operationally simple iron-catalyzed reductive cross-coupling reaction between aryl halides and allyl electrophiles has been developed. The underlying domino process exhibits high versatility with respect to the allylic leaving group (acetate, tosylate, diethyl phosphate, methyl carbonate, trimethylsilanolate, methanethiolate, chloride, bromide) and high economic and environmental sustainability with respect to the catalyst system (0.2–5 ...

Allyl acetate Structure

2-Iodobenzonitrile Structure

2-Iodobenzonitrile

~%

3-(2-Cyanophenyl)prop-1-ene Structure

3-(2-Cyanopheny...

Allyl methyl carbonate Structure

Allyl methyl ca...

bromoanisole Structure

~71%

1-allyl-2-methoxybenzene Structure

1-allyl-2-metho...

diethyl allyl phosphate 98 Structure

diethyl allyl p...

bromoanisole Structure

~55%

1-allyl-2-methoxybenzene Structure

1-allyl-2-metho...

(E/Z)-1-methoxy-2-(prop-1-enyl)benzene Structure

(E/Z)-1-methoxy...

Trimethyl Allyloxysilane Structure

Trimethyl Allyl...

bromoanisole Structure

~71%

1-allyl-2-methoxybenzene Structure

1-allyl-2-metho...

(E/Z)-1-methoxy-2-(prop-1-enyl)benzene Structure

(E/Z)-1-methoxy...

bromoanisole Structure

allyl toluene-4-sulfonate Structure

allyl toluene-4...

~73%

1-allyl-2-methoxybenzene Structure

1-allyl-2-metho...

(E/Z)-1-methoxy-2-(prop-1-enyl)benzene Structure

(E/Z)-1-methoxy...

bromoanisole Structure

allyl bromide Structure

~75%

1-allyl-2-methoxybenzene Structure

1-allyl-2-metho...

(E/Z)-1-methoxy-2-(prop-1-enyl)benzene Structure

(E/Z)-1-methoxy...

bromoanisole Structure

ALLYL CHLORIDE Structure

~61%

1-allyl-2-methoxybenzene Structure

1-allyl-2-metho...

(E/Z)-1-methoxy-2-(prop-1-enyl)benzene Structure

(E/Z)-1-methoxy...

4-Bromoanisole Structure

Allyl acetate Structure

~74%

Estragole Structure

4-Bromoanisole Structure

Allyl Methyl Sulfide Structure

Allyl Methyl Sulfide

~63%

Estragole Structure

Allyl acetate Structure

2-Bromobenzonitrile Structure

2-Bromobenzonitrile

ISOPROPYLMAGNESIUM CHLORIDE Structure

ISOPROPYLMAGNES...

~25%

3-(2-Cyanophenyl)prop-1-ene Structure

3-(2-Cyanopheny...

Detail

4-Bromochlorobenzene Structure

4-Bromochlorobenzene

Allyl acetate Structure

~83%

3-(4-CHLOROPHENYL)-1-PROPENE Structure

3-(4-CHLOROPHEN...

3-Bromopyridine Structure

3-Bromopyridine

Allyl acetate Structure

~48%

3-prop-2-enylpyridine Structure

3-prop-2-enylpy...

Allyl Methyl Sulfide Structure

Allyl Methyl Sulfide

1-Bromo-4-tert-butylbenzene Structure

1-Bromo-4-tert-...

~63%

3-(4-TERT-BUTYLPHENYL)-1-PROPENE Structure

3-(4-TERT-BUTYL...

Allyl acetate Structure

1-Bromo-4-tert-butylbenzene Structure

1-Bromo-4-tert-...

~67%

3-(4-TERT-BUTYLPHENYL)-1-PROPENE Structure

3-(4-TERT-BUTYL...

Allyl acetate Structure

1-Bromo-4-tert-butylbenzene Structure

1-Bromo-4-tert-...

~47%

3-(4-TERT-BUTYLPHENYL)-1-PROPENE Structure

3-(4-TERT-BUTYL...

1-tert-butyl-4-prop-1-enylbenzene Structure

1-tert-butyl-4-...

1-Bromo-4-tert-butylbenzene Structure

1-Bromo-4-tert-...

allyl toluene-4-sulfonate Structure

allyl toluene-4...

~62%

3-(4-TERT-BUTYLPHENYL)-1-PROPENE Structure

3-(4-TERT-BUTYL...

1-tert-butyl-4-prop-1-enylbenzene Structure

1-tert-butyl-4-...

1-Bromo-4-tert-butylbenzene Structure

1-Bromo-4-tert-...

allyl bromide Structure

~65%

3-(4-TERT-BUTYLPHENYL)-1-PROPENE Structure

3-(4-TERT-BUTYL...

1-tert-butyl-4-prop-1-enylbenzene Structure

1-tert-butyl-4-...

o-tolylmagnesium bromide Structure

o-tolylmagnesiu...

allyl bromide Structure

~77%

Benzene,1-methyl-2-(2-propen-1-yl)- Structure

Benzene,1-methy...

Allyl methyl carbonate Structure

Allyl methyl ca...

2-Bromotoluene Structure

~51%

Benzene,1-methyl-2-(2-propen-1-yl)- Structure

Benzene,1-methy...

Allyl acetate Structure

4-Bromo-1,2-difluorobenzene Structure

4-Bromo-1,2-dif...

~73%

3-(3,4-DIFLUOROPHENYL)-1-PROPENE Structure

3-(3,4-DIFLUORO...

4-Bromoanisole Structure

allyl bromide Structure

~0%

Estragole Structure

cis-Anethol Structure

4-Bromoanisole Structure

ALLYL CHLORIDE Structure

~0%

Estragole Structure

cis-Anethol Structure

4-Bromoanisole Structure

allyl bromide Structure

~86%

Estragole Structure

cis-Anethol Structure

4-Bromoanisole Structure

ALLYL CHLORIDE Structure

~70%

Estragole Structure

cis-Anethol Structure

Allyl acetate Structure

1,3-Dibromobenzene Structure

1,3-Dibromobenzene

~58%

1-ALLYL-3-BROMOBENZENE Structure

1-ALLYL-3-BROMO...

Allyl acetate Structure

4-Bromo-N,N-dimethylaniline Structure

4-Bromo-N,N-dim...

~63%

Benzenamine,N,N-dimethyl-4-(2-propen-1-yl)- Structure

Benzenamine,N,N...

Allyl acetate Structure

1-Bromo-3,5-dimethylbenzene Structure

1-Bromo-3,5-dim...

~70%

3-(3,5-DIMETHYLPHENYL)-1-PROPENE Structure

3-(3,5-DIMETHYL...

Allyl acetate Structure

1-Bromo-4-tert-butylbenzene Structure

1-Bromo-4-tert-...

~0%

3-(4-TERT-BUTYLPHENYL)-1-PROPENE Structure

3-(4-TERT-BUTYL...

1-tert-butyl-4-prop-1-enylbenzene Structure

1-tert-butyl-4-...

1-Bromo-4-tert-butylbenzene Structure

1-Bromo-4-tert-...

allyl toluene-4-sulfonate Structure

allyl toluene-4...

~0%

3-(4-TERT-BUTYLPHENYL)-1-PROPENE Structure

3-(4-TERT-BUTYL...

1-tert-butyl-4-prop-1-enylbenzene Structure

1-tert-butyl-4-...

1-Bromo-4-tert-butylbenzene Structure

1-Bromo-4-tert-...

allyl bromide Structure

~0%

3-(4-TERT-BUTYLPHENYL)-1-PROPENE Structure

3-(4-TERT-BUTYL...

1-tert-butyl-4-prop-1-enylbenzene Structure

1-tert-butyl-4-...

Bromobenzene Structure

Allyl acetate Structure

~70%

Allylbenzene Structure

Propargyl acetate Structure

Propargyl acetate

4-Bromotoluene Structure

~36%

1-methyl-4-propa-1,2-dienylbenzene Structure

1-methyl-4-prop...

1-allyl-2-methoxybenzene Structure

1-allyl-2-metho...

~%

1-Methoxy-2-propylbenzene Structure

1-Methoxy-2-pro...

Allyl Methyl Sulfide Structure

Allyl Methyl Sulfide

4-Bromotoluene Structure

~72%

1-allyl-4-methylbenzene Structure

1-allyl-4-methy...

diethyl allyl phosphate 98 Structure

diethyl allyl p...

4-Bromotoluene Structure

~59%

1-allyl-4-methylbenzene Structure

1-allyl-4-methy...

1-(1-Propenyl)-4-methylbenzene Structure

1-(1-Propenyl)-...

4-Bromotoluene Structure

allyl bromide Structure

~69%

1-allyl-4-methylbenzene Structure

1-allyl-4-methy...

1-(1-Propenyl)-4-methylbenzene Structure

1-(1-Propenyl)-...

Allyl acetate Structure

2-Bromobenzonitrile Structure

2-Bromobenzonitrile

ISOPROPYLMAGNESIUM CHLORIDE Structure

ISOPROPYLMAGNES...

~20%

3-(2-Cyanophenyl)prop-1-ene Structure

3-(2-Cyanopheny...

Detail

4-Bromoanisole Structure

Prenyl acetate Structure

~%

1-methoxy-4-(2-methylbut-3-en-2-yl)benzene Structure

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

1-methoxy-4-(3-methylbut-2-enyl)benzene Structure

1-methoxy-4-(3-...

diethyl allyl phosphate 98 Structure

diethyl allyl p...

4-Bromotoluene Structure

~0%

1-allyl-4-methylbenzene Structure

1-allyl-4-methy...

1-(1-Propenyl)-4-methylbenzene Structure

1-(1-Propenyl)-...

Allyl acetate Structure

4-Bromotoluene Structure

~15%

1-allyl-4-methylbenzene Structure

1-allyl-4-methy...

1-(1-Propenyl)-4-methylbenzene Structure

1-(1-Propenyl)-...

4-Bromotoluene Structure

allyl bromide Structure

~0%

1-allyl-4-methylbenzene Structure

1-allyl-4-methy...

1-(1-Propenyl)-4-methylbenzene Structure

1-(1-Propenyl)-...

Allyl acetate Structure

1-Bromo-4-fluorobenzene Structure

1-Bromo-4-fluor...

~65%

3-(4-FLUOROPHENYL)-1-PROPENE Structure

3-(4-FLUOROPHEN...

1-fluoro-4-(prop-1-enyl)benzene Structure

1-fluoro-4-(pro...

4-Bromoanisole Structure

3-Buten-2-yl Acetate Structure

3-Buten-2-yl Acetate

~%

1-(but-2-en-1-yl)-4-methoxybenzene Structure

1-(but-2-en-1-y...

1-but-3-en-2-yl-4-methoxybenzene Structure

1-but-3-en-2-yl...

Intramolecular hydroamination of unbiased and functionalized...

[Julian, Lisa D.; Hartwig, John F. Journal of the American Chemical Society, 2010 , vol. 132, # 39 p. 13813 - 13822]

Functionalized arylzinc compounds in ethereal solvent: Direc...

[Ikegami, Ryo; Koresawa, Akiko; Shibata, Takanori; Takagi, Kentaro Journal of Organic Chemistry, 2003 , vol. 68, # 6 p. 2195 - 2199]

Cobalt-catalyzed direct electrochemical cross-coupling betwe...

[Gomes, Paulo; Gosmini, Corinne; Perichon, Jacques Journal of Organic Chemistry, 2003 , vol. 68, # 3 p. 1142 - 1145]

Photosubstitution of dicyanobenzenes by group 14 organometal...

[Mizuno, Kazuhiko; Nakanishi, Kazuhisa; Otsuji, Yoshio Chemistry Letters, 1988 , p. 1833 - 1836]

Photosubstitution of Dicyanobenzenes by Allylic Silanes, Ger...

[Nakanishi, Kazuhisa; Mizuno, Kazuhiko; Otsuji, Yoshio Bulletin of the Chemical Society of Japan, 1993 , vol. 66, # 8 p. 2371 - 2379]