925-90-6

Basic information

• Product Name: ETHYLMAGNESIUM BROMIDE
• Synonyms: bromoethyl-magnesiu;ethvlmagnesiumbromide;ETHYLMAGNESIUM BROMIDE;bromoethylmagnesium;Ethylmagnesium;ETHYLMAGNESIUM BROMIDE SOLUTION, ~3 M IN;ETHYLMAGNESIUM BROMIDE, 1.0M SOLUTION IN TETRAHYDROFURAN;ETHYLMAGNESIUM BROMIDE, 3.0M SOLUTION IN DIETHYL ETHER
• CAS NO: 925-90-6
• Molecular Formula: C₂H₅BrMg
• Molecular Weight: 133.27
• EINECS: 213-127-3
• Product Categories: Classes of Metal Compounds;Grignard Reagents;Grignard Reagents & Alkyl Metals;Mg (Magnesium) Compounds;Synthetic Organic Chemistry;Typical Metal Compounds;AlkylChemical Synthesis;Grignard Reagents;Organic Bases;Organometallic Reagents;Synthetic Reagents;grignard reagent;Alkyl;Chemical Synthesis;Organometallic Reagents
• Mol File: 925-90-6.mol
• Article Data: 76

Chemical Properties

• Melting Point: -116.3°C
• Boiling Point: 34.6°C
• Flash Point: <−30 °F
• Appearance: Pale yellow to brown/Solution
• Density: 1.02 g/mL at 25 °C
• Storage Temp.: water-free area
• Solubility: Miscible in alcohols, ketones, esters, ethers, hydrocarbons.
• Water Solubility: Reacts with water.
• Sensitive: Air & Moisture Sensitive
• BRN: 3587203
• CAS DataBase Reference: ETHYLMAGNESIUM BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYLMAGNESIUM BROMIDE(925-90-6)
• EPA Substance Registry System: ETHYLMAGNESIUM BROMIDE(925-90-6)

Safety Data

• Hazard Codes: F+,C,F
• Statements: 12-14/15-19-22-34-66-67-40-11-14-37
• Safety Statements: 16-26-36/37/39-43-45-7/8-27-9
• RIDADR: UN 3399 4.3/PG 1
• WGK Germany: 1
• F: 1-3-10
• TSCA: Yes
• HazardClass: 4.3
• PackingGroup: I
• Hazardous Substances Data: 925-90-6(Hazardous Substances Data)

Usage

Chemical Properties

Ethylmagnesium bromide is generally sold as a dark brown solution and can be dissolved in diethyl ether, butyl ether, isopropyl ether, THF and anisole.

Uses

Ethylmagnesium Bromide is a useful reagent in preparation of zirconium complexes having two phenoxy-imine chelate ligands for olefin polymerization.

Preparation

Ethylmagnesium bromide is commercially available, usually as a solution in diethyl ether or tetrahydrofuran. It may be prepared in the normal manner of Grignard reagents — by reacting bromoethane with magnesium in diethyl ether: EtBr + Mg → EtMgBr

Reactions

Ethylmagnesium bromide reacts with water to produce ethane.CH3CH2MgBr+H2O→CH3-CH3+Mg(OH)BrReaction of ethylmagnesium bromide with ethyl acetate in the presence of styrene and titanium(IV) isopropoxide as a catalyst leads to (Z)-1-methyl-2-phenylcyclopropanol in 42% yield.

General Description

Ethylmagnesium bromide, an organomagnesium compound, is commonly known as Grignard reagent. It is a powerful carbon nucleophile mainly used for C-C bond formation. Ethylmagnesium bromide solution (3.0 M in diethyl ether) can be used for copper(I)-catalyzed allylic substitution reaction.Grignard reagents are organometallic compounds discovered by a French chemist, Victor Grignard in 1900. These compounds can be obtained as a formula “RMgX” by the reaction of halogenated hydrocarbons with magnesium metal in anhydrous solvents such as diethyl ether,1) and have been widely used in organic synthesis.

Hazard

Flammable, dangerous fire risk.

InChI:InChI=1/C2H5.BrH.Mg/c1-2;;/h1H2,2H3;1H;/q;;+1/p-1/rC2H5BrMg/c1-2-4-3/h2H2,1H3

Synthetic route

ethyl bromide (74-96-4) → ethylmagnesium bromide (925-90-6)

Conditions	Yield
With magnesium In tetrahydrofuran at 18℃; for 0.125h; Inert atmosphere; Flow reactor;	98%
With magnesium In diethyl ether at 25℃; under 5171.62 Torr; Solvent; Concentration; Inert atmosphere; Flow reactor;	96%
With magnesium In diethyl ether at 26.9℃; Mechanism; Thermodynamic data; Eact, various solvents;

ethylene dibromide (106-93-4) → ethylmagnesium bromide (925-90-6)

Conditions	Yield
With magnesium In tetrahydrofuran at 20℃; for 4h; Inert atmosphere;	83%

pentaethyldigermane (993-84-0) + di-tert-butyl peroxide (110-05-4) → tetraethyldigermane (52119-02-5) + ((CH3CH2)2Ge)4 (79411-55-5) + ethylmagnesium bromide (925-90-6) + octaethyltrigermane (13937-05-8)

Conditions	Yield
In benzene Irradiation (UV/VIS); digermane soln. irradiating in the presence of an excess of t-Bu2O2; product content detd. by high-pressure chromy.;	A 34% B 3% C 11% D 26%

bromomagnesium tetraethylborate tetrahydrofuran complex → triethyl borane (97-94-9) + ethylmagnesium bromide (925-90-6)

Conditions	Yield
In diethyl ether Et4BMgBr*4THF in ether stirred at 25°C for 6 h; not isolated; detected by NMR;	A 20% B 20%

ethyl bromide (74-96-4) + 9,10-dihydro-9,10-anthracendiyl-tris(THF)magnesium (86901-19-1) → 9-ethyl-9,10-dihydroanthracene (605-82-3) + 9,10-diethyl-9,10-dihydro-anthracene (46868-29-5) + 1,2-Diaethyl-1,2-dihydro-anthracen (94960-49-3) + ethylmagnesium bromide (925-90-6) + 2-ethyl-1,2-dihydroanthracene (126694-96-0) + 1,4-Diethyl-1,4-dihydro-anthracene (126694-84-6)

Conditions	Yield
In toluene for 1h; Ambient temperature; other primary, secondary and tertiary alkyl, aryl, allyl, propargyl and benzyl halides; other solvents, other molar ratios RX/1; other temperatures; other reaction times;

ethyl bromide (74-96-4) + 9,10-dihydro-9,10-anthracendiyl-tris(THF)magnesium (86901-19-1) → 9-ethyl-9,10-dihydroanthracene (605-82-3) + 9,10-diethyl-9,10-dihydro-anthracene (46868-29-5) + ethylmagnesium bromide (925-90-6) + 2-ethyl-1,2-dihydroanthracene (126694-96-0)

Conditions	Yield
In diethyl ether for 16h; Ambient temperature; Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;

ethyl bromide (74-96-4) → 9-ethyl-9,10-dihydroanthracene (605-82-3) + 9,10-diethyl-9,10-dihydro-anthracene (46868-29-5) + ethylmagnesium bromide (925-90-6) + 2-ethyl-1,2-dihydroanthracene (126694-96-0)

Conditions	Yield
With magnesium anthracene * 3 THF In toluene for 1h; Ambient temperature; Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;

diethyl ether (60-29-7) + triethyllead bromide (41141-89-3) + magnesium copper-alloy → ethylmagnesium bromide (925-90-6) + tetraethyllead(IV) (78-00-2) + lead

diethyl ether (60-29-7) + triethyllead bromide (41141-89-3) + magnesium → ethylmagnesium bromide (925-90-6) + tetraethyllead(IV) (78-00-2) + lead

ethyl bromide (74-96-4) + magnesium (7439-95-4) → ethylmagnesium bromide (925-90-6)

Conditions	Yield
In diethyl ether at 20 - 30℃;

ethyl iodide (75-03-6) → ethylmagnesium bromide (925-90-6)

Conditions	Yield
With iodine; magnesium In diethyl ether Inert atmosphere;

ethyl bromide (74-96-4) + magnesium → ethylmagnesium bromide (925-90-6)

Conditions	Yield
With diethyl ether

m-bromobenzoic aldehyde (3132-99-8) + ethylmagnesium bromide (925-90-6) → (+/-)-1-(3-bromophenyl)propanol (74157-47-4)

Conditions	Yield
In diethyl ether at -78 - 20℃;	100%
In diethyl ether	92%
Stage #1: m-bromobenzoic aldehyde; ethylmagnesium bromide In diethyl ether for 1.08333h; Cooling with ice; Stage #2: With hydrogenchloride In diethyl ether; water	88%

ethylmagnesium bromide (925-90-6) + benzaldehyde (100-52-7) → 1-Phenyl-1-propanol (93-54-9)

Conditions	Yield
With methylaluminum bis(2,6-di-tert-butylphenoxide) In diethyl ether; toluene at -78℃; for 2h;	100%
In diethyl ether at 0 - 20℃;	87%
Stage #1: ethylmagnesium bromide; benzaldehyde In tetrahydrofuran at 30℃; for 24h; Inert atmosphere; Stage #2: With water In tetrahydrofuran Inert atmosphere;	73%

ethylmagnesium bromide (925-90-6) + cyclohexanone (108-94-1) → 1-ethylcyclohexanol (1940-18-7)

Conditions	Yield
With methylaluminum bis(2,6-di-tert-butylphenoxide) In diethyl ether; toluene at -78℃; for 2h;	100%
In diethyl ether at 0 - 20℃;	90%
In diethyl ether; benzene
In diethyl ether

4-Trifluoromethylbenzaldehyde (455-19-6) + ethylmagnesium bromide (925-90-6) → (+/-)-1-<4-(trifluoromethyl)phenyl>-1-propanol (67081-98-5)

Conditions	Yield
In tetrahydrofuran for 2h; Ambient temperature;	100%
In diethyl ether for 2h; Ambient temperature;	93.7%
In diethyl ether Ambient temperature;	89%

2-formylbenzo[b]furan (4265-16-1) + ethylmagnesium bromide (925-90-6) → 1-(benzofuran-2-yl)propan-1-ol (220087-23-0)

Conditions	Yield
In tetrahydrofuran; diethyl ether at 20℃; for 4h; Inert atmosphere;	100%
In tetrahydrofuran; diethyl ether at -20℃; for 2h;

ethylmagnesium bromide (925-90-6) + 3,4-dihydro-6-methoxy-1-(4-methoxyphenyl)-2-naphthalenecarboxaldehyde (79822-58-5) → 1-<6-methoxy-1-(p-methoxyphenyl)-3,4-dihydro-2-naphthalenyl>propan-1-ol (79822-60-9)

Conditions	Yield
In diethyl ether 1.) overnight, 2.) reflux, 2 h;	100%

ethylmagnesium bromide (925-90-6) + 5-Bromo-1,1-dimethyl-1H-indene (124369-45-5) → 1,1-dimethyl-5-ethylind-2-ene (124369-46-6)

Conditions	Yield
With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In diethyl ether for 16h; Heating;	100%

ethylmagnesium bromide (925-90-6) + 2-(pentafluorophenyl)-4,4-dimethyl-2-oxazoline (90619-70-8) → 2-(2,6-diethyl-F-phenyl)-4,4-dimethyl-2-oxazoline

Conditions	Yield
In benzene Heating;	100%

ethylmagnesium bromide (925-90-6) + (S)-4-Benzyloxymethoxy-1-((S)-4,4-dimethyl-[1,3]dioxolan-2-yl)-pentan-3-one → (3S,4S)-4-Benzyloxymethoxy-1-((S)-4,4-dimethyl-[1,3]dioxolan-2-yl)-3-ethyl-pentan-3-ol

Conditions	Yield
In tetrahydrofuran at -93℃;	100%

ethylmagnesium bromide (925-90-6) + (2S,6R)-2-benzyloxymethoxy-7-(4-methoxybenzyloxy)-6-methoxyethoxymethoxyheptan-3-one (96823-35-7) → (2S,3R,6R)-2-benzyloxymethoxy-3-ethyl-7-(4-methoxybenzyloxy)-6-methoxyethoxymethoxyheptan-3-ol (96823-36-8)

Conditions	Yield
In tetrahydrofuran at -78℃; for 2h;	100%
In tetrahydrofuran at -78℃; for 1.5h; Yield given;

ethylmagnesium bromide (925-90-6) + 6-hydroxy-7-methyl-1-(phenylsulfinyl)spirononane-3,2'-<1,3>dioxolane>-9-one (145095-35-8) → 9-ethyl-6,9-dihydroxy-7-methyl-1-(phenylsulfinyl)-spirononane-3,2'-<1,3>dioxolane> (145095-38-1)

Conditions	Yield
With chloro-trimethyl-silane In tetrahydrofuran; diethyl ether at -78℃; for 0.25h;	100%

ethylmagnesium bromide (925-90-6) + (2R,5S)-5-benzyloxy-2-<(4S)-2,2-dimethyl-1,3-dioxolan-4-yl>heptan-4-one (144900-82-3) → (2R,4R,5S)-5-Benzyloxy-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-ethyl-heptan-4-ol (144534-88-3)

Conditions	Yield
In tetrahydrofuran at -78℃;	100%

ethylmagnesium bromide (925-90-6) + (2S,6S)-2-benzyloxymethoxy-6,7-isopropylidenedioxyheptan-3-one (110653-67-3) → (2S,3R,6S)-2-benzyloxymethoxy-3-ethyl-6,7-isopropylidenedioxyheptan-3-ol (113643-39-3)

Conditions	Yield
In tetrahydrofuran at -93℃; for 2h;	100%

ethylmagnesium bromide (925-90-6) + (2S,3S,4S,5Z)-3-(tert-butyldimethylsiloxy)-6-chloro-2,4-dimethyl-5-hexenal → (4R,5S,6S,7Z)-5-(tert-butyldimethylsiloxy)-8-chloro-4,6-dimethyl-7-octen-3-ol

Conditions	Yield
In tetrahydrofuran at -78℃;	100%
	96%

ethylmagnesium bromide (925-90-6) + 2-(F-phenyl)-4,4,6-trimethyl-5,6-dihydro-4H-oxazine (90619-68-4) → 2-(2,6-diethyl-F-phenyl)-4,4,6-trimethyl-5,6-dihydro-4H-oxazine

Conditions	Yield
In benzene for 10h; Heating;	100%

ethylmagnesium bromide (925-90-6) + 6-methoxy-1-(p-methoxyphenyl)-1,2,3,4-tetrahydro-2-naphthaldehyde (79830-30-1) → 1-<6-methoxy-1-(p-methoxyphenyl)-1,2,3,4-tetrahydro-2-naphthalenyl>propan-1-ol (79822-63-2)

Conditions	Yield
In diethyl ether 1.) overnight, 2.) reflux, 2 h;	100%

ethylmagnesium bromide (925-90-6) + ethyl-2-(dimethylphenylsilyl)pent-4-enoate (155366-60-2) → 4-(dimethylphenylsilyl)hept-6-en-3-one (155366-79-3)

Conditions	Yield
In tetrahydrofuran for 3h; Heating;	100%
In tetrahydrofuran for 3h; Heating;

ethylmagnesium bromide (925-90-6) + ethyl-2-pent-4-enoate (155366-61-3) → 4-hept-6-en-3-one (155366-80-6)

Conditions	Yield
In tetrahydrofuran for 3h; Heating;	100%
In tetrahydrofuran for 3h; Heating;

ethylmagnesium bromide (925-90-6) + (S)-N-methoxy-N-methyl-3-triisopropylsilanyloxy-2-methylpropionamide (158783-85-8) → (S)-1-triisopropylsilanyloxy-2-methyl-3-pentanone (158783-76-7)

Conditions	Yield
In tetrahydrofuran at 20℃; for 1.5h;	100%
In tetrahydrofuran at 0 - 20℃; for 2h;	89%

ethylmagnesium bromide (925-90-6) + ortho-bromobenzaldehyde (6630-33-7) → 1-(2-bromophenyl)propan-1-ol (74532-85-7)

Conditions	Yield
Stage #1: ethylmagnesium bromide; ortho-bromobenzaldehyde In tetrahydrofuran at -70 - 20℃; for 6h; Stage #2: With water; ammonium chloride In tetrahydrofuran	100%
In diethyl ether at 0 - 20℃;	95%
In tetrahydrofuran; diethyl ether at -78 - 0℃; Inert atmosphere;	81%

ethylmagnesium bromide (925-90-6) + 6H-benzo[c]thiochromen-6-one (4445-36-7) → 10-Ethyl-10H-9-thia-phenanthren-10-ol (87221-20-3)

Conditions	Yield
In tetrahydrofuran for 0.5h; Heating;	100%

ethylmagnesium bromide (925-90-6) + (S)-2-[(4R,5S,6S)-2,2-Di-tert-butyl-6-((S)-1-[1,3]dithiolan-2-yl-ethyl)-5-methyl-[1,3,2]dioxasilinan-4-yl]-propionaldehyde (193416-15-8) → (R)-2-[(4S,5S,6S)-2,2-Di-tert-butyl-6-((S)-1-[1,3]dithiolan-2-yl-ethyl)-5-methyl-[1,3,2]dioxasilinan-4-yl]-pentan-3-ol (193416-27-2)

Conditions	Yield
In diethyl ether at -78℃; for 2.5h;	100%

ethylmagnesium bromide (925-90-6) + (3aS,7R,7aS)-7-Methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-one (229307-84-0) → 3-[(R)-((4S,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-methoxy-methyl]-pentan-3-ol (264891-32-9)

Conditions	Yield
In tetrahydrofuran at 0℃; Alkylation;	100%

ethylmagnesium bromide (925-90-6) + N-methoxy-N-methyl-4-(1H-pyrrol-1-yl)butanamide (292067-21-1) → 6-(1H-pyrrol-1-yl)hexan-6-one (292067-24-4)

Conditions	Yield
In diethyl ether at 18℃; for 2h;	100%
Stage #1: ethylmagnesium bromide; N-methoxy-N-methyl-4-(1H-pyrrol-1-yl)butanamide In diethyl ether at 18℃; for 1h; Stage #2: With potassium hydrogensulfate In diethyl ether at -40℃; for 0.1h; Further stages.;	95%
In diethyl ether at 18℃; for 1h; Grignard reaction;
In tetrahydrofuran at 0 - 20℃; for 2.5h; Inert atmosphere; Schlenk technique;
In diethyl ether at 0℃; for 1h; Inert atmosphere; Sealed tube;	7.09 g

ethylmagnesium bromide (925-90-6) + (E)-2-methyl-1,3-diphenyl-2-(p-tolylsulfinyl)aziridine (119487-86-4, 122406-30-8, 122406-40-0) → C15H14BrMgN

Conditions	Yield
In tetrahydrofuran at -78 - 20℃; Metallation;	100%

ethylmagnesium bromide (925-90-6) + 5-tert-butyldimethylsilyloxypentanal (87184-80-3) → 7-(tert-butyl-dimethyl-silanyloxy)-heptan-3-ol

Conditions	Yield
	100%
Stage #1: ethylmagnesium bromide; 5-tert-butyldimethylsilyloxypentanal In diethyl ether at 0℃; for 0.5h; Inert atmosphere; Stage #2: With hydrogenchloride In diethyl ether; water Inert atmosphere;
In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere;

5-bromo-3,4-dihydro-2H-pyran (26274-19-1) + ethylmagnesium bromide (925-90-6) → 5-ethyl-3,4-dihydropyran (15990-75-7)

Conditions	Yield
With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In tetrahydrofuran	100%

ethylmagnesium bromide (925-90-6) + 2,2'-(2,3-dimethoxy-1,4-phenylene)bis(4,4-dimethyl-2-oxazoline) (179693-93-7) → 2,2'-(2,3-diethyl-1,4-phenylene)bis(4,4-dimethyl-2-oxazoline) (179693-94-8)

Conditions	Yield
In tetrahydrofuran at 20℃; for 2h;	100%
In tetrahydrofuran; water	1.98 g (100%)

ethylmagnesium bromide (925-90-6) + 2β-carbo-N-methoxy-N-methylamino-3α-(3,4-dichlorophenyl)-7β-methoxymethoxy-8-methyl-8-azabicyclo[3.2.1]octane → 1-[3α-(3,4-dichlorophenyl)-7β-methoxymethoxy-8-methyl-8-azabicyclo[3.2.1]oct-2-yl]propan-1-one

Conditions	Yield
In tetrahydrofuran at 0 - 22℃;	100%

ethylmagnesium bromide (925-90-6) + 2-((tert-butyl(diphenyl)silyl)oxy)acetic acid ethyl ester (441784-83-4) → 1-(((tert-butyldiphenylsilyl)oxy)methyl)cyclopropan-1-ol

Conditions	Yield
Stage #1: ethylmagnesium bromide; 2-((tert-butyl(diphenyl)silyl)oxy)acetic acid ethyl ester With titanium(IV) isopropylate In tetrahydrofuran at 20℃; for 12h; Stage #2: With ammonium chloride In tetrahydrofuran	100%
Stage #1: ethylmagnesium bromide; 2-((tert-butyl(diphenyl)silyl)oxy)acetic acid ethyl ester With titanium(IV) isopropylate In tetrahydrofuran at 20℃; Stage #2: With water In tetrahydrofuran	97%
With titanium(IV) isopropylate In tetrahydrofuran at -10 - 25℃; for 5h; Kulinkovich cyclopropanation;	80%

Upstream product

• 74-96-4 ethyl bromide 
• 7439-95-4 magnesium 
• 993-84-0 pentaethyldigermane 
• 110-05-4 di-tert-butyl peroxide 
• 106-93-4 ethylene dibromide 
• 86901-19-1 9,10-dihydro-9,10-anthracendiyl-tris(THF)magnesium 
• 75-03-6 ethyl iodide 
• 60-29-7 diethyl ether 
• 41141-89-3 triethyllead bromide 

Downstream Products

• 108300-13-6 (+/-)-2-phenyl-1-tropane-3endo-yl-butan-2-ol 
• 71-36-3 butan-1-ol 
• 71-41-0 pentan-1-ol 
• 627-18-9 1-bromo-3-propanol 
• 590-36-3 2-methylpentan-2-ol 
• 595-41-5 2,3-dimethyl-3-pentanol 
• 615-29-2 4-methyl-3-hexanol 
• 928-95-0 (E)-2-Hexen-1-ol 
• 688-99-3 5-hexen-3-ol 
• 53045-70-8 2-ethylbut-3-en-1-ol 
• 3944-13-6 1,1-Diaethyl-silacyclopentan 
• 18035-51-3 1,1'-diethyl-1,1'-oxy-bis-silolane 
• 31535-06-5 trans-3-chloro-2-ethyltetrahydropyran 
• 31535-06-5 cis-3-chloro-2-ethyltetrahydropyran 

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