3333-13-9

Basic information

• Product Name: 1-ALLYL-4-METHYLBENZENE
• Synonyms: 1-ALLYL-4-METHYLBENZENE;3-(4-METHYLPHENYL)-1-PROPENE;1-methyl-4-(2-propenyl)-benzen;1-methyl-4-(2-propenyl)-benzene;1-methyl-4-allylbenzene;1-propene,3-(4-methylphenyl)-;3-p-Tolylpropene;4-Allyltoluene
• CAS NO: 3333-13-9
• Molecular Formula: C₁₀H₁₂
• Molecular Weight: 132.2
• EINECS: 222-063-5
• Product Categories: Acyclic;Alkenes;Building Blocks;Chemical Synthesis;Organic Building Blocks
• Mol File: 3333-13-9.mol
• Article Data: 50

Chemical Properties

• Melting Point: 240 °C
• Boiling Point: 182.7 °C at 760 mmHg
• Flash Point: 54°C
• Appearance: /
• Density: 0.865g/mLat 25℃
• Vapor Pressure: 1.09mmHg at 25°C
• Refractive Index: n20/D 1.509
• CAS DataBase Reference: 1-ALLYL-4-METHYLBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ALLYL-4-METHYLBENZENE(3333-13-9)
• EPA Substance Registry System: 1-ALLYL-4-METHYLBENZENE(3333-13-9)

Safety Data

• Hazard Codes: T,Xn
• Statements: 10-22
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 3333-13-9(Hazardous Substances Data)

Usage

General Description

1-ALLYL-4-METHYLBENZENE, also known as para-allyl toluene, is an organic compound with the chemical formula C10H12. It is a colorless liquid with a strong, sweet odor, and it is commonly used as a flavor and fragrance ingredient. It is found in various essential oils such as ylang-ylang, jasmine, and hyacinth. 1-ALLYL-4-METHYLBENZENE is also used in the production of perfumes, soaps, and other cosmetic products. It is important to handle this chemical with care as it can cause skin and eye irritation, and it may be harmful if swallowed or inhaled. In addition, it is flammable and should be stored and handled in a well-ventilated area.

InChI:InChI=1/C10H12/c1-3-4-10-7-5-9(2)6-8-10/h3,5-8H,1,4H2,2H3

Synthetic route

Allyl acetate (591-87-7) + 4-tolyltrimethylstannane (937-12-2) → p-allyltoluene (3333-13-9)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In N,N,N,N,N,N-hexamethylphosphoric triamide for 6h;	100%
tetrakis(triphenylphosphine) palladium(0) In N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃;	100 % Chromat.

vinyl magnesium bromide (1826-67-1) + 4-Methylbenzyl bromide (104-81-4) → p-allyltoluene (3333-13-9)

Conditions	Yield
With copper(l) iodide In tetrahydrofuran at -30℃; for 1h;	93%

allyl bromide (106-95-6) + pTolSnR3 → p-allyltoluene (3333-13-9)

Conditions	Yield
Pd(phenylimino)acenaphthene dimethyl fumarate In N,N-dimethyl-formamide at 50℃; for 16h;	88%

2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (72824-04-5) + benzyl chloride (100-44-7) → p-allyltoluene (3333-13-9)

Conditions	Yield
Stage #1: 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; benzyl chloride With tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine; cesium fluoride In dichloromethane at 30℃; for 20h; Inert atmosphere; Stage #2: With toluene-4-sulfonic acid In dichloromethane at 30℃; for 10h; Inert atmosphere; regioselective reaction;	80%

4-tolyltrimethylstannane (937-12-2) + allyl bromide (106-95-6) → p-allyltoluene (3333-13-9)

Conditions	Yield
bis(η3-allyl-μ-chloropalladium(II)) In N,N-dimethyl-formamide at 70℃;	75%
With bis(η3-allyl-μ-chloropalladium(II)) In N,N-dimethyl-formamide at 70℃; for 3h;	75%

4-tolyltrimethylstannane (937-12-2) + allyl bromide (106-95-6) → p-allyltoluene (3333-13-9) + trimethyltin bromide (1066-44-0)

Conditions	Yield
With ((π-C3H5)PdCl)2 In N,N-dimethyl-formamide 70°C;	A 75% B n/a
tetrakis(triphenylphosphine) palladium(0) In N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; for 6h;	A 18 % Chromat. B n/a

para-bromotoluene (106-38-7) + allyl bromide (106-95-6) → p-allyltoluene (3333-13-9)

Conditions	Yield
With magnesium In tetrahydrofuran for 0.5h; Heating;	72%
(i) Mg, Et2O, (ii) /BRN= 605308/; Multistep reaction;
Stage #1: para-bromotoluene With iodine; magnesium In diethyl ether for 2h; Reflux; Inert atmosphere; Stage #2: allyl bromide In diethyl ether at 20℃; Cooling with ice; Inert atmosphere;

4-methylphenylboronic acid (5720-05-8) + 3-chloroprop-1-ene (107-05-1) → p-allyltoluene (3333-13-9)

Conditions	Yield
With potassium tert-butylate In isopropyl alcohol at 50℃; for 12h; Inert atmosphere;	68%

4-methylphenylboronic acid (5720-05-8) + allyl bromide (106-95-6) → p-allyltoluene (3333-13-9)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water for 6h; Reflux;	66%
With C25H19ClNOPPd; potassium carbonate In toluene at 90℃; for 24h;	56%
With potassium carbonate In toluene at 90℃; for 3h; regioselective reaction;	15%
With aluminum oxide; potassium fluoride; palladium at 100℃; for 4h; Suzuki reaction;	28 % Chromat.
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran at 0 - 50℃; Schlenk technique; Inert atmosphere;

4-tolyl iodide (624-31-7) + allyltrimethoxysilane (2551-83-9) → p-allyltoluene (3333-13-9)

Conditions	Yield
With tetrabutyl ammonium fluoride; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; N,N-dimethyl-formamide at 85℃; for 2h;	60%

allyltriethoxysilane (2550-04-1) + 4-tolyl iodide (624-31-7) → p-allyltoluene (3333-13-9)

Conditions	Yield
With palladium(II) acetylacetonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; tetrabutylammonium triphenyldifluorosilicate In tetrahydrofuran-d8 at 80℃; Hiyama Coupling; Glovebox; Sealed tube;	58%

Allyl acetate (591-87-7) + para-bromotoluene (106-38-7) → p-allyltoluene (3333-13-9)

Conditions	Yield
With magnesium; triphenylphosphine; copper(I) bromide; lithium bromide In tetrahydrofuran at 80℃; for 6h; Sealed tube;	56%
Stage #1: para-bromotoluene With magnesium; lithium chloride In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Stage #2: With iron(III)-acetylacetonate In tetrahydrofuran for 0.0833333h; Inert atmosphere; Stage #3: Allyl acetate In tetrahydrofuran at 0℃; for 0.75h; Inert atmosphere;

1-cyclopropyl-4-methyl-benzene (6921-43-3) → p-allyltoluene (3333-13-9) + (Z)-1-(4-tolyl)-1-propene (2077-29-4) + (E)-1-methyl-4-(prop-1-enyl)benzene (2077-30-7)

Conditions	Yield
With n-butyllithium; potassium tert-butylate In tetrahydrofuran 1) RT, 24 h, 2) reflux;	A 8% B 35% C 53%

para-chlorotoluene (106-43-4) + allyl-trimethyl-silane (762-72-1) → p-allyltoluene (3333-13-9)

Conditions	Yield
With caesium carbonate In 2,2,2-trifluoroethanol for 18h; Inert atmosphere; UV-irradiation;	53%

tri-n-butylstannylmethyl iodide (66222-29-5) + C15H15LiOS → p-allyltoluene (3333-13-9)

Conditions	Yield
In tetrahydrofuran Product distribution; investigation of reactions of allyl 2-pyridyl sulfides or allyl phenyl sulfones;	46%

C15H15LiOS → p-allyltoluene (3333-13-9)

Conditions	Yield
With tri-n-butylstannylmethyl iodide In tetrahydrofuran	46%

allyl iodid (556-56-9) + 4-methylphenylboronic acid (5720-05-8) → p-allyltoluene (3333-13-9)

Conditions	Yield
With aluminum oxide; potassium fluoride; palladium at 100℃; for 4h; Suzuki reaction;	39%

4-tolyl iodide (624-31-7) + 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (72824-04-5) → p-allyltoluene (3333-13-9)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In tetrahydrofuran at 80℃; for 48h; Suzuki-Miyaura coupling; Inert atmosphere;	35%

C28H28In(1-)*Mg(2+)*Cl(1-) + allyl bromide (106-95-6) → p-allyltoluene (3333-13-9)

Conditions	Yield
With [FeCl2(dpbz)2] at 85℃; for 4h;	21%

allyl bromide (106-95-6) + para-methylphenylmagnesium bromide (4294-57-9) → p-allyltoluene (3333-13-9)

Conditions	Yield
With diethyl ether

para-bromotoluene (106-38-7) + allyltributylstanane (24850-33-7) → p-allyltoluene (3333-13-9)

Conditions	Yield
Heating;

allyl iodid (556-56-9) + 4-tolyltrimethylstannane (937-12-2) → p-allyltoluene (3333-13-9)

Conditions	Yield
With <η3-C3H5Pd(PPh3)2>+*Cl- In N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; for 4h;	64 % Chromat.

allyl iodid (556-56-9) + 4-tolyltrimethylstannane (937-12-2) → p-allyltoluene (3333-13-9) + trimethylstannyl iodide (811-73-4)

Conditions	Yield
tetrakis(triphenylphosphine) palladium(0) In N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; for 6h;	A 56 % Chromat. B n/a

Allyl acetate (591-87-7) + 4-tolyltrimethylstannane (937-12-2) → p-allyltoluene (3333-13-9) + trimethyltin acetate (1118-14-5)

Conditions	Yield
tetrakis(triphenylphosphine) palladium(0) In N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; for 6h;	A 100 % Chromat. B n/a

4-tolyltrimethylstannane (937-12-2) → p-allyltoluene (3333-13-9) + (4,4'-dimethyl-1,1'-biphenyl) (613-33-2) + trimethyltin acetate (1118-14-5)

Conditions	Yield
With Allyl acetate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 68℃; for 2.5h;	A 59 % Chromat. B 32 % Chromat. C n/a

C18H17ClO4 (84648-35-1) → p-allyltoluene (3333-13-9) + p-n-propyltoluene (1074-55-1) + C16H17Cl (84648-45-3) + 3-Chloro-benzoic acid 3-p-tolyl-propyl ester (84648-39-5) + chlorobenzene (108-90-7)

Conditions	Yield
In cyclohexanone at 100℃; Mechanism; CIDNP, thermolyse;

C18H17ClO4 (84648-35-1) → p-allyltoluene (3333-13-9) + 1-(3-chloropropyl)-4-methylbenzene (77975-31-6) + C16H17Cl (84648-45-3) + 3-Chloro-benzoic acid 3-p-tolyl-propyl ester (84648-39-5) + 1,3-Dichlorobenzene (541-73-1)

Conditions	Yield
In various solvent(s) at 100℃; Mechanism; CIDNP, thermolyse;

allyl alcohol (107-18-6) + toluene (108-88-3) → p-allyltoluene (3333-13-9) + 1-methyl-2-(2-propenyl)-benzene (1587-04-8) + 1-allyl-3-methylbenzene (3333-20-8) + propene (187737-37-7) + ethene (74-85-1) + Allyl ether (557-40-4)

Conditions	Yield
HUSY26 at 149.9℃; Product distribution; other catalysts, other temp., also allylation with 3-buten-1-ol and allyl chloride;

(4-MeC6H4)Ti(O-i-Pr)3 (112176-19-9) + allyl bromide (106-95-6) → p-allyltoluene (3333-13-9)

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)) In diethyl ether; benzene for 0.5h;	98 % Chromat.

p-allyltoluene (3333-13-9) + aniline (62-53-3) → C15H15N

Conditions	Yield
With sodium sulfate In diethyl ether at 20℃; for 24h;	100%

p-allyltoluene (3333-13-9) + [4-(benzylideneamino)phenyl]methanol (783-08-4) → (E)-N-[4-(4-methylphenyl)-1-phenylbut-3-enyl]-4-methoxyaniline

Conditions	Yield
With sodium hexamethyldisilazane In 1,4-dioxane at 25℃; for 20h; Inert atmosphere; regioselective reaction;	99%

p-allyltoluene (3333-13-9) + methylthiol (74-93-1) → methyl(3-(p-tolyl)propyl)sulfane

Conditions	Yield
With C38H28Au2F12FeN2O8P2S4 In 1,4-dioxane at 45℃; for 20h; Inert atmosphere; Glovebox; Sealed tube;	98%

p-allyltoluene (3333-13-9) + ethene (74-85-1) → 1-ethenyl-4-methylbenzene (622-97-9)

Conditions	Yield
With Hoveyda-Grubbs catalyst second generation; di-μ-bromobis-(tritert-butylphosphine)dipalladium(I) In tetrahydrofuran at 60℃; under 7500.75 Torr; for 16h; Autoclave;	94%

p-allyltoluene (3333-13-9) + methyl dimethyl 2-(trifluoromethyl)propanedioate (5838-00-6) → (E)-dimethyl 2-(3-(p-tolyl)allyl)-2-(trifluoromethyl)malonate (1455396-80-1)

Conditions	Yield
With 2,6-dimethoxy-p-quinone; palladium diacetate; triphenylphosphine In 1-methyl-pyrrolidin-2-one at 20℃; for 12h; Inert atmosphere; Schlenk technique;	94%

p-allyltoluene (3333-13-9) + ethyl 2,2-difluoro-2-iodoacetate (7648-30-8) → 2,2-difluoro-4-iodo-5-(p-tolyl) pentanoate

Conditions	Yield
With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; bis-diphenylphosphinomethane In tetrahydrofuran at 80℃; for 20h; Catalytic behavior; Reagent/catalyst; Solvent; Inert atmosphere; Schlenk technique;	94%
With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; bis-diphenylphosphinomethane In tetrahydrofuran at 80℃; for 20h; Reagent/catalyst; Temperature; Inert atmosphere;	90%
With o-phenylenebis(diphenylphosphine); cobalt(II) bromide; zinc In water; acetone at 20℃; for 3h; Inert atmosphere; stereoselective reaction;	84%

p-allyltoluene (3333-13-9) → p-Tolylaceton (2096-86-8)

Conditions	Yield
With iron(III) sulfate; palladium(II) trifluoroacetate; sodium 2,2,2-trifluoroacetate In water; acetonitrile at 30℃; Wacker-Tsuji Olefin Oxidation; Inert atmosphere; Darkness;	94%

p-allyltoluene (3333-13-9) + ethyl-3,3,3-trifluoropyruvate (13081-18-0) → ethyl (2R,E)-2-(trifluoromethyl)-2-hydroxy-5-p-tolylpent-4-enoate

Conditions	Yield
With cis-Pd(S(-)-BINAP)(OTf)2 In dichloromethane at 20℃; for 0.166667h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	93%
With silver hexafluoroantimonate; chiral PtCl2 based NU-BIPHEP-type catalyst In dichloromethane for 60h;
silver hexafluoroantimonate; δ-dichloro[3,3'-bis(diphenylphosphanyl)-5,6,7,8,5',6',7',8'-octahydro[2,2']binaphthalene]platinum In dichloromethane at 20℃; for 1h; Product distribution / selectivity;	n/a

p-allyltoluene (3333-13-9) → 4'-methylpropiophenone (5337-93-9)

Conditions	Yield
With tert.-butylhydroperoxide; palladium diacetate; toluene-4-sulfonic acid In water; acetonitrile at 20℃; for 6h; Wacker Oxidation; chemoselective reaction;	93%

p-allyltoluene (3333-13-9) + 4-nitrobenzaldehdye (555-16-8) → (1R,2S)-1-(4-nitrophenyl)-2-(p-tolyl)but-3-en-1-ol

Conditions	Yield
Stage #1: p-allyltoluene With N-fluorobis(benzenesulfon)imide; triphenylphosphine; bis(dibenzylideneacetone)-palladium(0); bis((+)-pinanediolato)diboron In toluene at 50℃; for 24h; Inert atmosphere; Stage #2: 4-nitrobenzaldehdye With C34H21O4P In toluene at 25℃; for 24h; Inert atmosphere; enantioselective reaction;	91%

p-allyltoluene (3333-13-9) → 4-methyl-cinnamaldehyde (56578-35-9)

Conditions	Yield
With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dichloride In 1,2-dichloro-ethane at 50℃; for 2h; stereoselective reaction;	90%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dichloride In water; 1,2-dichloro-ethane at 50℃;	90%
With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,2-dichloro-ethane at 60℃; for 10h;	80%
With water; oxygen; palladium diacetate In dimethyl sulfoxide at 100℃; under 760.051 Torr; for 24h; Green chemistry; regioselective reaction;	78%

p-allyltoluene (3333-13-9) → (E)-1-(3-azidoprop-1-enyl)-4-methylbenzene

Conditions	Yield
With sodium azide; oxygen; palladium diacetate In dimethyl sulfoxide at 100℃; for 24h; regioselective reaction;	90%
Multi-step reaction with 2 steps 1: bromine / chloroform / 0.17 h / 0 °C 2: sodium azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium iodide / dimethyl sulfoxide / 2 h / 22 °C / Sealed tube View Scheme

p-allyltoluene (3333-13-9) + C12H13NO4 → (E)-3-methyl-3-(4-nitrophenyl)-6-(p-tolyl)hex-5-en-2-one

Conditions	Yield
With palladium diacetate; caesium carbonate; triphenylphosphine; tert-butyl alcohol In tetrahydrofuran at 80℃; for 22h; Schlenk technique; Inert atmosphere;	90%

p-allyltoluene (3333-13-9) + 2.5-Dimethyl-N.N.N'.N'-tetramethyl-p-phenylendiamin → C22H32N2

Conditions	Yield
With C32H53N2OScSi2; N,N'-dimethylaniliniumtetrakis(pentafluorophenyl)borate In toluene at 80℃; for 12h; Inert atmosphere; regioselective reaction;	90%

p-allyltoluene (3333-13-9) → 4-methylphenylacetaldehyde (104-09-6)

Conditions	Yield
Stage #1: p-allyltoluene With ozone In dichloromethane at -78℃; Stage #2: With (Z,Z,Z)-4,4'-bis[4-(diphenylphosphino)styryl]stilbene In dichloromethane at -78 - 23℃; for 0.5h; Stage #3: With erythrosine B In tetrahydrofuran for 1h; Irradiation;	89%
With ozone In methanol at -78℃; for 0.75h;	13%

p-allyltoluene (3333-13-9) + phenylsilane (694-53-1) → phenyl(1-p-tolylpropan-2-yl)silane

Conditions	Yield
Stage #1: phenylsilane With C22H31Cl2CoN2P In tetrahydrofuran for 0.166667h; Inert atmosphere; Glovebox; Stage #2: p-allyltoluene In tetrahydrofuran at 60℃; for 24h; Inert atmosphere; Sealed tube; regioselective reaction;	89%

p-allyltoluene (3333-13-9) + 4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane (78782-17-9) → (E)-4,4,5,5-tetramethyl-2-(4-(p-tolyl)but-3-en-1-yl)-1,3,2-dioxaborolane (1375536-65-4)

Conditions	Yield
With potassium dihydrogenphosphate; silver tetrafluoroborate; 1,2-Bis(phenylsulfinyl)ethane; palladium diacetate; [1,4]naphthoquinone In 1,4-dioxane at 50℃; for 24h; Sealed tube; Schlenk technique;	88%

p-allyltoluene (3333-13-9) + dimethyl sulfoxide (67-68-5) → 1-(methylthio)-3-p-tolylpropan-2-ol

Conditions	Yield
With ammonium iodide; water at 130℃; for 24h; Schlenk technique;	88%

p-allyltoluene (3333-13-9) + 4-Hydroxyquinazoline (491-36-1) → 3-(3-(p-tolyl)allyl)quinazolin-4(3H)-one

Conditions	Yield
With 2,6-dimethyl-1,4-benzoquinone; palladium dichloride In dimethyl sulfoxide at 100℃; for 24h; chemoselective reaction;	88%

p-allyltoluene (3333-13-9) + 2-bromo-2,2-difluoro-N-phenyl-acetamide (127427-45-6) → 2,2-difluoro-4-hydroxy-N-phenyl-5-(p-tolyl)pentanamide

Conditions	Yield
With N,N,N',N'',N'''-pentamethyldiethylenetriamine; rhodamine 6G at 25℃; for 22h; Irradiation;	88%

p-allyltoluene (3333-13-9) + 1-Methylbenzimidazole (1632-83-3) → 1-methyl-2-(3-(p-tolyl)propyl)-1H-benzo[d]imidazole + 1-methyl-2-(1-(p-tolyl)propyl)-1H-benzo[d]imidazole

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); [1,3-bis(2,4,6-trimethylphenyl)imidazol]-2-ylidene In toluene at 130℃; for 16h; Overall yield = 94 %; regioselective reaction;	A n/a B 87%
With bis(1,5-cyclooctadiene)nickel(0); trimethylaluminum; 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene In toluene at 130℃; for 16h; Overall yield = 89 %; regioselective reaction;	A 85% B n/a

p-allyltoluene (3333-13-9) → 1-bromo-7-methylnaphthalene (7511-27-5)

Conditions	Yield
With carbon tetrabromide; iron In ethanol at 20℃; for 2h; Irradiation;	87%

p-allyltoluene (3333-13-9) → p-methylcinnamyl alcohol (122058-30-4)

Conditions	Yield
With palladium(II) trifluoroacetate; water; p-benzoquinone In dimethyl sulfoxide at 20℃; for 22h; Sealed tube; Green chemistry; regioselective reaction;	86%
With hydrogenchloride; water; oxygen; palladium dichloride In dimethyl sulfoxide at 100℃; under 760.051 Torr; for 24h; Green chemistry; regioselective reaction;	81%

p-allyltoluene (3333-13-9) + 1-(((dimethyl(oxo)- λ6-sulfanylidene)methyl)sulfonyl)-4-methylbenzene → (2E,4E)-1,5-di-p-tolylpenta-2,4-dien-1-one

Conditions	Yield
With 2,6-dimethyl-1,4-benzoquinone; palladium diacetate; triphenylphosphine In dimethyl sulfoxide at 65℃; for 24h; regioselective reaction;	85%

p-allyltoluene (3333-13-9) + 1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) → (E)-1-((3-(p-tolyl)allyl)oxy)pyrrolidine-2,5-dione

Conditions	Yield
With oxygen; palladium diacetate; copper(II) acetate monohydrate; acetic acid In acetonitrile at 75℃;	85%

p-allyltoluene (3333-13-9) + trifluoromethane sulfonyl chloride (421-83-0) → 4,4,4-trifluoro-1-(p-tolyl)butane-2-sulfonyl chloride

Conditions	Yield
With dipotassium hydrogenphosphate; [Cu(2,9-bis(4-methoxyphenyl)-1,10-phenanthroline)2]Cl In acetonitrile at 20℃; for 24h; Inert atmosphere; Irradiation;	82%

p-allyltoluene (3333-13-9) + butan-1-ol (71-36-3) → (E)-n-butyl 3-(p-tolyl)acrylate (123248-21-5)

Conditions	Yield
With water; oxygen; palladium diacetate In N,N-dimethyl acetamide at 100℃; under 760.051 Torr; for 24h; Schlenk technique; chemoselective reaction;	82%

Upstream product

• 106-95-6 allyl bromide 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 556-56-9 allyl iodid 
• 937-12-2 4-tolyltrimethylstannane 
• 84648-35-1 C₁₈H₁₇ClO₄ 
• 762-72-1 allyl-trimethyl-silane 
• 6729-59-5 tris(2-methylphenyl)bismuth difluoride 
• 107-05-1 3-chloroprop-1-ene 
• 60-29-7 diethyl ether 
• 106-38-7 para-bromotoluene 
• 109-64-8 1,3-dibromo-propane 
• 5720-05-8 4-methylphenylboronic acid 
• 624-31-7 4-tolyl iodide 
• 72824-04-5 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 103859-80-9 1-methyl-4-(2,4,4,4-tetrachloro-butyl)-benzene 
• 339555-80-5 1,4-Di-p-tolyl-2-buten 
• 2077-29-4 (Z)-1-(4-tolyl)-1-propene 
• 2077-30-7 (E)-1-methyl-4-(prop-1-enyl)benzene 
• 2698-14-8 1-methyl-4-(prop-1-enyl)benzene 
• 187737-37-7 propene 
• 74-85-1 ethene 
• 106-42-3 para-xylene 
• 108-88-3 toluene 
• 4957-14-6 4,4'-dimethyldiphenylmethane 
• 77134-00-0 3-(4-methylphenyl)prop-2-enyl acetate 
• 28446-70-0 (E)-4-methylcinnamonitrile 
• 1315611-33-6 1-fluoro-4-(-2-(4-methylbenzyl)cyclopropyl)benzene 

Relevant articles and documents

Aryl C-F bond functionalization preparation method

The invention relates to the technical field of organic compound synthesis, in particular to an aryl C-F bond functionalization preparation method. A fluorobenzene compound and a nucleophilic reagent react under the action of a composite catalyst, wherein the composite catalyst is formed by mixing a visible light catalyst and a metal catalyst. The photocatalyst is adopted, the reaction process is safe and controllable, and operation in the preparation and production process is simplified; a purple LED is used as a reaction energy source and is green and environment-friendly, the energy utilization rate is high, and conversion from light energy to chemical energy can be efficiently realized; in the reaction, a simple nucleophilic reagent is used for attacking free radical cation species generated under a visible light catalysis condition, so that a target product with an extremely wide range is efficiently and greenly prepared; the operation steps are simplified, and the reaction route is shortened; and moreover, the forward reaction rate is high, and the production efficiency is remarkably improved.

Palladium-Catalyzed Oxidative Allylation of Sulfoxonium Ylides: Regioselective Synthesis of Conjugated Dienones

The first examples of palladium-catalyzed allylic C-H oxidative allylation of sulfoxonium ylides to afford the corresponding conjugated dienones with moderate to good yields have been established. The features of this novel conversion include mild reaction conditions, wide substrate scope, and excellent regioselectivity.

SO2 conversion to sulfones: Development and mechanistic insights of a sulfonylative Hiyama cross-coupling

A Pd-catalyzed Hiyama cross-coupling reaction using SO2 is described. The use of silicon-based nucleophiles leads to the formation of allyl sulfones under mild conditions with a broad functional group tolerance. Control experiments coupled with DFT calculations shed light on the key steps of the reaction mechanism, revealing the crucial role of a transient sulfinate anion.