3874-54-2

Basic information

• Product Name: 4-Chloro-4'-fluorobutyrophenone
• Synonyms: 3-CHLOROPROPYL4-FLUOROPHENYLKETONE/4-CHLORO-4''-FLUOROBUTYROPHENONE;1-Butanone, 4-chloro-1-(4-fluorophenyl)-;1-(4-Fluorophenyl)-4-chloro-1-butanone;γ-Chloro-4'-fluorobutyrophenone;ω-Chloro-4'-fluorobutyrophenone;4-Chloro-4'-fluorobu;4-chloro-4-fluorophenyl ketone;1-Chloro-4-(4-fluorophenyl)-4-oxobutane
• CAS NO: 3874-54-2
• Molecular Formula: C₁₀H₁₀ClFO
• Molecular Weight: 200.64
• EINECS: 223-395-3
• Product Categories: ketone;Fluorobenzene;C10;Carbonyl Compounds;Ketones;Aromatics;Miscellaneous Reagents;API Intermediate
• Mol File: 3874-54-2.mol
• Article Data: 19

Chemical Properties

• Melting Point: 5-6 °C
• Boiling Point: 130-132 °C (0.97513 mmHg)
• Flash Point: >230 °F
• Appearance: Slightly yellow-greenish clear/Oil
• Density: 1.22 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.5255(lit.)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Sparingly), Ethyl Acetate (Slightly), Methanol (Slightly)
• Water Solubility: 0.38 g/L (20 ºC)
• BRN: 608741
• CAS DataBase Reference: 4-Chloro-4'-fluorobutyrophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-4'-fluorobutyrophenone(3874-54-2)
• EPA Substance Registry System: 4-Chloro-4'-fluorobutyrophenone(3874-54-2)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-20/21/22
• Safety Statements: 24/25-36-26
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 3874-54-2(Hazardous Substances Data)

Usage

Description

4-Chloro-4'-fluorobutyrophenone, with the chemical formula C10H10ClFNO and CAS number 3874-54-2, is an organic compound that serves as a valuable intermediate in the synthesis of various organic molecules. Its unique structure, featuring a chlorine and a fluorine atom attached to a butyrophenone backbone, endows it with specific reactivity and properties that make it suitable for a range of applications in organic chemistry.

Uses

Used in Organic Synthesis:
4-Chloro-4'-fluorobutyrophenone is used as a synthetic intermediate for the preparation of a variety of organic compounds. Its presence of electron-withdrawing chlorine and fluorine atoms influences the reactivity of the molecule, making it a versatile building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Chloro-4'-fluorobutyrophenone is utilized as a key component in the development of new drugs. Its unique structure allows for the creation of novel molecular entities with potential therapeutic applications, contributing to the advancement of medicine and the treatment of various diseases.
Used in Agrochemical Industry:
4-Chloro-4'-fluorobutyrophenone also finds application in the agrochemical sector, where it is employed in the synthesis of new pesticides and other crop protection agents. Its chemical properties enable the design of innovative compounds that can effectively control pests and diseases, thereby enhancing crop yields and food security.
Used in Specialty Chemicals:
In the specialty chemicals market, 4-Chloro-4'-fluorobutyrophenone is used as a precursor for the production of various high-value chemicals. Its unique combination of functional groups allows for the creation of tailored compounds with specific properties, catering to the needs of diverse industries such as materials science, coatings, and fragrances.

Synthetic route

fluorobenzene (462-06-6) + 4-Chlorobutanoyl chloride (4635-59-0) → 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2)

Conditions	Yield
With aluminum (III) chloride In dichloromethane at 20℃; for 4h; Time;	90%
With aluminium trichloride In carbon disulfide at 20℃; for 2h;	73.2%
With aluminium trichloride

4-chloro-1-(4-fluorophenyl)-1,1-(ethylenedioxy)butane (3308-94-9) → 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2)

Conditions	Yield
In(OSO2CF3)3 In acetone at 100℃; for 0.0833333h; microwave irradiation;	89%

4-flourophenylmagnesium bromide (352-13-6) + 4-Chlorobutanoyl chloride (4635-59-0) → 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2)

Conditions	Yield
Stage #1: 4-Chlorobutanoyl chloride With 1-methyl-pyrrolidin-2-one In toluene at 0℃; for 0.5h; Stage #2: 4-flourophenylmagnesium bromide In tetrahydrofuran; toluene at -10 - 0℃; for 4.25h; chemoselective reaction;	88%

1-(4-chlorobut-1-yn-1-yl)-4-fluorobenzene (1183278-95-6) → 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2)

Conditions	Yield
With iron(III) chloride; water; silver(I) triflimide In 1,4-dioxane for 18h; regioselective reaction;	85%
With water; bis(trifluoromethanesulfonyl)amide In 1,4-dioxane at 100℃;	85%
With water In 1,4-dioxane at 80 - 120℃; regioselective reaction;	85%

1-(4-fluorophenyl)cyclobutan-1-ol (339365-53-6) → 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2)

Conditions	Yield
With manganese(II) triflate; tetrabutylammonium acetate; acetic acid; magnesium chloride In acetonitrile at 25℃; for 3.5h; Inert atmosphere; Electrochemical reaction; Sealed tube;	84%
With 1,10-Phenanthroline; tert-butylhypochlorite; silver trifluoromethanesulfonate In acetonitrile at 20℃; for 6h; Inert atmosphere; Schlenk technique; regioselective reaction;	81%

4-chlorobutyraldehyde (6139-84-0) + 1-Bromo-4-fluorobenzene (460-00-4) → 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2)

Conditions	Yield
With Quinuclidine; 4,4'-di-tert-butyl-2,2'-bipyridine nickel(II) bromide; [Ir(C6H2F2-C5H3NCF3)2(4,4′-di-tert-butyl-2,2′-dipyridyl)]; potassium carbonate In 1,4-dioxane at 20℃; for 20h; Inert atmosphere; Sealed tube; Irradiation;	77%
With palladium diacetate; 9,10-phenanthrenequinone; potassium hydrogencarbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In acetone at 20℃; for 24h; Reagent/catalyst; Irradiation;	71%

1-iodo-3-chloro-propane (6940-76-7) + 4-fluoroboronic acid (1765-93-1) + molybdenum hexacarbonyl (13939-06-5, 199620-15-0) → 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2)

Conditions	Yield
Stage #1: 1-iodo-3-chloro-propane; 4-fluoroboronic acid With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; benzene at 20℃; for 24h; Suzuki-Miyaura Coupling; Inert atmosphere; Irradiation; Stage #2: molybdenum hexacarbonyl With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 70℃; Suzuki-Miyaura Coupling; Inert atmosphere;	68%

1-ethynyl-4-fluorobenzene (766-98-3) + 3-chloropropionyl peroxide (19263-25-3) → 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2)

Conditions	Yield
With iron(III) trifluoromethanesulfonate; trifluorormethanesulfonic acid In tetrahydrofuran at 70 - 80℃; for 12.25h; Inert atmosphere; Schlenk technique;	60%

3-chloro-4'-fluoropropiophenone (347-93-3) + diethyl 4-chloromethyl-1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylate (3613-34-1) → 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2)

Conditions	Yield
With manganese; di-tert-butyl peroxide; α,α,α-trifluorotoluene at 100℃; for 48h; Inert atmosphere;	51%

1-Bromo-4-fluorobenzene (460-00-4) → 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: iodine; magnesium / tetrahydrofuran / Inert atmosphere; Reflux; Sealed tube 1.2: 0 - 20 °C / Inert atmosphere; Sealed tube 2.1: acetic acid; manganese(II) triflate; magnesium chloride; tetrabutylammonium acetate / acetonitrile / 3.5 h / 25 °C / Inert atmosphere; Electrochemical reaction; Sealed tube View Scheme

para-thiocresol (106-45-6) + 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → 1-(4-fluorophenyl)-4-(p-tolylthio)butan-1-one (132427-90-8)

Conditions	Yield
	100%
With triethylamine In tetrahydrofuran for 16h; Ambient temperature;	99%

N-methoxylamine hydrochloride (593-56-6) + 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → 4-chloro-1-(4-fluorophenyl)butan-1-one O-methyl oxime (1352950-38-9)

Conditions	Yield
With pyridine at 20℃;	100%

4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → cyclopropyl(4-fluorophenyl)methanone (772-31-6)

Conditions	Yield
With sodium hydroxide In water at 60℃; for 5h;	100%

toluene-3-thiol (108-40-7) + 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → 1-(Fluorophenyl)-4-(3-methylphenylthio)-1-butanone

Conditions	Yield
With triethylamine In tetrahydrofuran	99%
With triethylamine In tetrahydrofuran	99%

toluene-3-thiol (108-40-7) + 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → 1-(4-Fluorophenyl)-4-(3-methylphenylthio)-1-butanone

Conditions	Yield
With triethylamine In tetrahydrofuran	99%

ethylene glycol (107-21-1) + 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → 4-chloro-1-(4-fluorophenyl)-1,1-(ethylenedioxy)butane (3308-94-9)

Conditions	Yield
With toluene-4-sulfonic acid In water; toluene for 16h; Inert atmosphere; Reflux;	98%
With toluene-4-sulfonic acid In benzene for 18h; Heating;	93%
With toluene-4-sulfonic acid In benzene for 15h; Heating;	90%

4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) + 1-(2,5-dimethylphenyl)piperazine (1013-25-8) → 4-[4-(2,5-dimethylphenyl)piperazin-1-yl]-1-(4-fluorophenyl)butan-1-one

Conditions	Yield
With sodium hydrogencarbonate; sodium iodide In acetonitrile for 22h; Reflux;	96%

4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → (+/-)-4-chloro-1-(4-fluorophenyl)butan-1-ol (51787-87-2)

Conditions	Yield
With sodium tetrahydroborate In ethanol at 0℃; for 7h;	95%
With sodium tetrahydroborate In ethanol at 0 - 20℃; for 3h;	94%
With sodium tetrahydroborate In ethanol at 0 - 20℃; for 12h;	93%

4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → 1-iodo-3-(p-fluorophenylcarbonyl)propane (40862-32-6)

Conditions	Yield
With sodium iodide In butanone for 3h; Heating;	95%
With sodium iodide In acetone for 24h; Reflux;	92%
With sodium iodide In acetone for 16h; Reflux;	77%
In sodium iodide; butanone
With sodium iodide In [(2)H6]acetone for 8h; Reflux;

4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → 4-(n-butyl)fluorobenzene (20651-65-4)

Conditions	Yield
With nickel In tetrahydrofuran for 15h; Heating;	95%

4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → C10H10FN3O (154440-76-3)

Conditions	Yield
With sodium azide In N,N-dimethyl-formamide	95%
With sodium azide; potassium iodide In N,N-dimethyl-formamide at 90℃;

4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) + (S)-2-methylpropane-2-sulfinamide (343338-28-3) → (S,E)-N-(4-chloro-1-(4-fluorophenyl)butylidene)-2-methylpropane-2-sulfinamide (1218989-31-1)

Conditions	Yield
With titanium (IV) ethoxide In tetrahydrofuran at 65℃; for 48h; Inert atmosphere;	94%

4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → C10H11FO

Conditions	Yield
Stage #1: 4-(4-fluorophenyl)-4-oxo-n-butyl chloride With C32H33FeN3O2Si; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In toluene at -40 - 20℃; for 2h; Schlenk technique; Glovebox; Stage #2: With potassium carbonate In methanol; toluene at 20℃; for 12h; Schlenk technique; Glovebox; enantioselective reaction;	94%

4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) + 1-Phenyl-1,3,8-triaza-spiro[4.5]decan-4-one (1021-25-6) → spiperone (749-02-0)

Conditions	Yield
With diisopropylamine In N,N-dimethyl-formamide at 80℃; for 17h; Inert atmosphere;	93%
With triethylamine; potassium iodide In acetonitrile for 20h; Heating;	74%
With triethylamine; potassium iodide In acetonitrile for 20h; Inert atmosphere; Reflux;	63%

4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) + potassium thioacetate (10387-40-3) → S-(4-(4-fluorophenyl)-4-oxobutyl) ethanethioate

Conditions	Yield
In N,N-dimethyl-formamide at 0 - 20℃; for 10h; Inert atmosphere;	92%

4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → (1R)-(+)-4-chloro-1-(4-fluorophenyl)butan-1-ol (126640-11-7)

Conditions	Yield
With B-chlorodiisopinocampheylborane In diethyl ether at -25℃; for 16h;	90%
With C22H27Cl2CoN3O; sodium triethylborohydride; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; enantioselective reaction;	87%
Stage #1: 4-(4-fluorophenyl)-4-oxo-n-butyl chloride With Triethoxysilane; (S,E)-(+)-2,6-diisopropyl-N-(2-((2-(4-phenyl-4,5-dihydrooxazol-2-yl)phenyl)amino)benzylidene)aniline; sodium triethylborohydride; cobalt(II) chloride In tetrahydrofuran; dichloromethane at 20℃; for 15h; Schlenk technique; Inert atmosphere; Stage #2: With potassium carbonate In tetrahydrofuran; methanol; dichloromethane at 20℃; for 2h; Schlenk technique; Inert atmosphere; enantioselective reaction;	75%
Multi-step reaction with 2 steps 1: 81 percent / NaBH4 / methanol / 4 °C View Scheme
With B-chlorodiisopinocampheylborane In tetrahydrofuran; diethyl ether; 2,2'-iminobis[ethanol] at 25℃;

4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → (1S)-(-)-4-chloro-1-(4-fluorophenyl)butan-1-ol (126640-10-6)

Conditions	Yield
With (-)-diisopinocamphenylborane chloride In diethyl ether at -25℃; for 16h;	90%
Multi-step reaction with 2 steps 1: 81 percent / NaBH4 / methanol / 4 °C View Scheme
With (-)-diisopinocamphenylborane chloride In tetrahydrofuran; diethyl ether; 2,2'-iminobis[ethanol] at 25℃;

4-fluorobenzylic alcohol (459-56-3) + 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → cyclopropyl-[4-(4-fluoro-benzyloxy)-phenyl]-methanone (868699-44-9)

Conditions	Yield
With tetrabutylammomium bromide; sodium hydride In tetrahydrofuran at 30℃; for 18h;	90%

4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → (-)-4-chloro-1-(4-fluorophenyl)butan-1-ol

Conditions	Yield
Stage #1: 4-(4-fluorophenyl)-4-oxo-n-butyl chloride With (S)-2,2',6,6'-tetramethoxy-4,4'-bis(diphenylphosphino)-3,3'-bipyridine; phenylsilane; copper(II) acetate monohydrate In toluene at -20 - 20℃; for 48h; Stage #2: With hydrogenchloride In water; toluene Reagent/catalyst; enantioselective reaction;	90%

fluoroiodomethane (373-53-5) + 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → 5-chloro-1-fluoro-2-(4-fluorophenyl)pentan-2-ol

Conditions	Yield
With methyllithium lithium bromide In tetrahydrofuran; diethyl ether at -78℃; for 0.0833333h; Inert atmosphere;	90%

1-phenylmethylpiperazine (2759-28-6) + 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → cyclopropyl-{4-(4-benzylpiperazin-1-yl)phenyl}methanone

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 140℃;	90%

4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → 1-(4-chlorobutyl)-4-fluorobenzene (54540-58-8)

Conditions	Yield
With triethylsilane; trifluoroacetic acid at 0℃; for 2h;	89%
With hydrogen; palladium on activated charcoal In ethanol
With hydrogenchloride; mercury dichloride; zinc In toluene for 5h; Reflux;
With triethylsilane In trifluoroacetic acid

4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) + 4-flourophenylmagnesium bromide (352-13-6) → δ-Hydroxy-δ-bis(p-fluorophenyl)butyl chloride (51787-80-5)

Conditions	Yield
In diethyl ether Heating;	88.4%

4-hydroxy-4-phenylpiperidin (40807-61-2) + 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → 1-(4-fluorophenyl)-4-(4-hydroxy-4-phenylpiperidin-1-yl)butan-1-one (3109-12-4)

Conditions	Yield
With sodium hydrogencarbonate; potassium iodide In toluene for 24h; Reflux;	88%
With potassium iodate; potassium carbonate In toluene Inert atmosphere;	27%
With toluene; potassium iodide

4-(4-chlorophenyl)-4-hydroxypiperidine (39512-49-7) + 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → haloperidol (52-86-8)

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile at 75℃; for 24h; Temperature;	88%
With potassium iodide In toluene for 45h; Reflux;	85%
With potassium iodide In toluene at 130℃; for 45h; Sealed tube;	79%

1-(4-chlorophenyl)-1,4-diazepane (41885-98-7) + 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → 4-(4-(4-chlorophenyl)-1,4-diazepan-1-yl)-1-(4-fluorophenyl)butan-1-one

Conditions	Yield
With potassium carbonate; potassium iodide In 1,2-dimethoxyethane for 18h; Heating;	87%

[bis(acetoxy)iodo]benzene (3240-34-4) + 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → C12H12ClFO3 (1394244-16-6)

Conditions	Yield
With tetrabutylammomium bromide; potassium hydroxide In 1,4-dioxane at 20℃; for 1h;	87%

Upstream product

• 462-06-6 fluorobenzene 
• 4635-59-0 4-Chlorobutanoyl chloride 
• 3308-94-9 4-chloro-1-(4-fluorophenyl)-1,1-(ethylenedioxy)butane 
• 347-93-3 3-chloro-4'-fluoropropiophenone 
• 3613-34-1 diethyl 4-chloromethyl-1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylate 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 766-98-3 1-ethynyl-4-fluorobenzene 
• 19263-25-3 3-chloropropionyl peroxide 
• 6940-76-7 1-iodo-3-chloro-propane 
• 1765-93-1 4-fluoroboronic acid 
• 13939-06-5 molybdenum hexacarbonyl 
• 339365-53-6 1-(4-fluorophenyl)cyclobutan-1-ol 
• 1183278-95-6 1-(4-chlorobut-1-yn-1-yl)-4-fluorobenzene 
• 352-13-6 4-flourophenylmagnesium bromide 

Downstream Products

• 3109-12-4 4-(4-hydroxy-4-phenyl-1-piperidinyl)-1-(4-fluorophenyl)-1-butanone 
• 21492-58-0 4-(2,3-dihydro-5H-benzo[f][1,4]oxazepin-4-yl)-1-(4-fluoro-phenyl)-butan-1-one 
• 54981-16-7 9-[4-(4-fluoro-phenyl)-4-oxo-butyl]-5-methyl-1-oxa-3,9-diaza-spiro[5.5]undecan-2-one 
• 73962-25-1 1-[4-(4-Fluoro-phenyl)-4-oxo-butyl]-4-(2-methoxymethoxy-phenyl)-piperidine-4-carbonitrile 
• 112933-68-3 (S)-1-Cyclopropyl-1-(4-fluoro-phenyl)-2-methanesulfinyl-ethanol 
• 51787-84-9 4-(1,4-dioxa-8-azaspiro<4.5>dec-8-yl)-4'-fluorobutyrophenone 
• 170921-52-5 8-[4-(4-fluoro-phenyl)-4-oxo-butyl]-1,3,8-triaza-spiro[4.5]decan-4-one 
• 36116-18-4 cyclopropyl 4-hydroxyphenyl ketone 
• 54161-57-8 1-(4-chloro-1,1-diethoxy-butyl)-4-fluoro-benzene 
• 327617-79-8 2-(4-fluoro-phenyl)-tetrahydro-furan-2-carboxylic acid 

Relevant articles and documents

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The invention belongs to the technical field of medicine preparation, and particularly relates to a preparation method of flupiperidinol. The preparation method of the fluoropiperidinol, provided by the invention, comprises the following steps of providing 4-(4-chlorphenyl)-4-piperidinol of which the purity is 99% or above, providing 4-chloro-1-(4-fluorophenyl)butan-1-one of which the purity is more than 99%, mixing the 4-(4-chlorphenyl)-4-piperidinol, 4-chloro-1-(4-fluorophenyl)butan-1-one, an alkaline substance and a catalyst, and carrying out a first substitution reaction to obtain a crudeproduct, and mixing the crude product with an organic solvent, and sequentially carrying out reflux and crystallization to obtain the flupiperidinol. The flupiperidinol prepared according to the preparation method provided by the invention has relatively high yield and purity.

Mn-Enabled Radical-Based Alkyl-Alkyl Cross-Coupling Reaction from 4-Alkyl-1,4-dihydropyridines

Highly efficient alkylation of β-chloro ketones and their derivatives was achieved by means of domino dehydrochlorination/Mn-enabled radical-based alkyl-alkyl cross-coupling reaction. In situ-generated α,β-unsaturated ketones and their analogues were identified as the reaction intermediates. Known bioactive compounds, such as melperone and azaperone, could be easily prepared from β-chloropropiophenone in two steps.

Direct Aldehyde C-H Arylation and Alkylation via the Combination of Nickel, Hydrogen Atom Transfer, and Photoredox Catalysis

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