2083-91-2

Basic information

• Product Name: N,N-Dimethyltrimethylsilylamine
• Synonyms: DIMETHYLAMINOTRIMETHYLSILAN;(DIMETHYLAMINO)TRIMETHYLSILANE;N,N-DIMETHYLAMINOTRIMETHYLSILANE;N,N-DIMETHYLAMINOTRIMETHYLSILANE TMSDMA;N,N-DIMETHYLTRIMETHYLSILYLAMINE;N-TRIMETHYLSILYDIMETHYLAMINE;N-(TRIMETHYLSILYL)DIMETHYLAMINE;TMSDMA
• CAS NO: 2083-91-2
• Molecular Formula: C₅H₁₅NSi
• Molecular Weight: 117.26
• EINECS: 218-222-3
• Product Categories: Aminosilanes;Analytical Chemistry;GC Derivatizing Reagents;Si (Classes of Silicon Compounds);Silicon Compounds (for Synthesis);Silylation (GC Derivatizing Reagents);Si-N Compounds;Synthetic Organic Chemistry;Trimethylsilylation (GC Derivatizing Reagents);Derivatization Reagents GC;Reagents for Silylation;Silylation Reagents;Analytical Reagents;Analytical/Chromatography;Building Blocks;Chemical Synthesis;Derivatization Reagents;Nitrogen Compounds;Organic Building Blocks;Protected Amines
• Mol File: 2083-91-2.mol
• Article Data: 27

Chemical Properties

• Melting Point: <0°C
• Boiling Point: 84 °C(lit.)
• Flash Point: −3 °F
• Appearance: clear colorless to pale yellow liquid
• Density: 0.732 g/mL at 25 °C(lit.)
• Vapor Pressure: 4.11mmHg at 25°C
• Refractive Index: n20/D 1.397(lit.)
• Storage Temp.: Flammables area
• PKA: 10.77±0.70(Predicted)
• Water Solubility: Decomposition
• Sensitive: Moisture Sensitive
• BRN: 1731861
• CAS DataBase Reference: N,N-Dimethyltrimethylsilylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-Dimethyltrimethylsilylamine(2083-91-2)
• EPA Substance Registry System: N,N-Dimethyltrimethylsilylamine(2083-91-2)

Safety Data

• Hazard Codes: F,C
• Statements: 11-34
• Safety Statements: 16-26-36/37/39-45
• RIDADR: UN 2733 3/PG 2
• WGK Germany: 3
• F: 1-10
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 2083-91-2(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to pale yellow liquid

Uses

N,N-Dimethyltrimethylsilylamine was used in the synthesis of phosphoramidite. It was also employed as a reagent in the preparation of iminium salts and amides as well as for the silylation of polymers. A combination of N-(trimethylsilyl)dimethylamine and MeI was also effective to give p-methylbenzoic acid with a 85% yield based on 90% conversion from the corresponding Me ester. DETA has been treated with N-(trimethylsilyl)-dimethylamine to yield mono-, di- and tri- silylated derivatives

InChI:InChI=1/C7H21NSi2/c1-8(9(2,3)4)10(5,6)7/h1-7H3

Synthetic route

dimethyl amine (124-40-3) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → N,N-Dimethyltrimethylsilylamine (2083-91-2)

Conditions	Yield
With 1,3-dimethyl-2-imidazolidinone at 40℃; Reagent/catalyst;	94%
With ammonium sulfate at 80℃; for 8h; Reagent/catalyst; Time; Autoclave;	84%

trimethylsilyl <(dimethylamino)methyl>methylcarbamate (91749-17-6) → 1,3,5-trimethyl-1,3,5-triazacyclohexane (108-74-7) + N,N-Dimethyltrimethylsilylamine (2083-91-2)

Conditions	Yield
at 20℃; for 360h; nitrogen atmosphere;	A 90% B n/a

bis-(dimethylamino)methane (51-80-9) + bis(trimethylsilyl) 2-(2-furyl)ethylphosphonite (333364-16-2) → N,N-Dimethyltrimethylsilylamine (2083-91-2) + O-trimethylsilyl-[2-(2-furyl)ethyl](dimethylaminomethyl)phosphinate

Conditions	Yield
With zinc(II) chloride at 130℃; for 1h;	A n/a B 83%

benzylthiotrimethylsilane (14629-67-5) + N,N-dimethylphenylmethane sulfenamide (107427-35-0) → dibenzyl disulphide (150-60-7) + N,N-Dimethyltrimethylsilylamine (2083-91-2)

Conditions	Yield
at 80 - 110℃;	A 72% B 79%

trimethylsilyl iodide (16029-98-4) + N,N-dimethyl acetamide (127-19-5) → N,N-Dimethyltrimethylsilylamine (2083-91-2) + heptamethyldisilazane (920-68-3) + N-methyldiacetamide (1113-68-4) + methyl iodide (74-88-4)

Conditions	Yield
In dichloromethane at 35℃; for 5h;	A 76% B 1% C 5% D 3%

chloro-trimethyl-silane (75-77-4) + dimethyl amine (124-40-3) → N,N-Dimethyltrimethylsilylamine (2083-91-2)

Conditions	Yield
In methylbutane Ambient temperature;	75%
In octane; acetonitrile at 20℃; for 5h; Solvent; Reflux;	70%

bis-(dimethylamino)methane (51-80-9) + bis(trimethylsilyl) [2-(2-furyl)-1-(trimethylsilyloxycarbonyl)ethyl]phosphonite (333361-87-8) → N,N-Dimethyltrimethylsilylamine (2083-91-2) + trimethylsilyl (dimethylaminomethyl)[2-(2-furyl)-1-(trimethylsiloxycarbonyl)ethyl]phosphinate (333361-89-0)

Conditions	Yield
With zinc(II) chloride at 110 - 130℃; for 1.5h;	A n/a B 74%

N,N-dimethyl-P,P-dipropylphosphinous amide → N,N-Dimethyltrimethylsilylamine (2083-91-2) + dipropylphosphinous iodide (81373-58-2)

Conditions	Yield
With trimethylsilyl iodide In chlorobenzene at 110 - 132℃; for 8h;	A n/a B 63%

trimethylsilyl iodide (16029-98-4) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → N,N-Dimethyltrimethylsilylamine (2083-91-2) + N-formyl-N-methylformamide (18197-25-6) + N-Methyl-N-(trimethylsilyl)-formamid (13889-02-6) + formyl iodide (50398-22-6) + methyl iodide (74-88-4)

Conditions	Yield
In dichloromethane at 40℃; for 5h;	A 61% B 1% C 11% D 5% E 11%

trimethylsilyl iodide (16029-98-4) + Hexamethylphosphorous triamide (1608-26-0) → N,N-Dimethyltrimethylsilylamine (2083-91-2) + N,N,N',N'-tetramethylphosphorodiamidous iodide (20502-38-9)

Conditions	Yield
In dichloromethane Ambient temperature;	A n/a B 60%

bis-(dimethylamino)methane (51-80-9) + C7H19PS4Si (153080-50-3) → N,N-Dimethyltrimethylsilylamine (2083-91-2) + Tetrathiophosphoric acid dimethylaminomethyl ester diethyl ester

Conditions	Yield
at 100℃; for 1h;	A 57% B n/a
at 90 - 100℃;

methyl-bis(dimethylamino)phosphine (14937-39-4) + trimethylsilylazide (4648-54-8) → N,N-Dimethyltrimethylsilylamine (2083-91-2) + N-trimethylsilyl-methylbis(dimethylaminophosphine) imine (82181-74-6) + C11H33N5P2Si (82181-79-1)

Conditions	Yield
at 100℃; for 16h;	A n/a B 45% C 8.0 g
at 100℃; for 16h;	A n/a B 45% C 20%
at 100℃; for 16h;	A n/a B 45% C 8 g

N-(trimethylsilylmethyl)methylamine (18135-05-2) → N,N-Dimethyltrimethylsilylamine (2083-91-2)

Conditions	Yield
With n-butyllithium; hexane In tetrahydrofuran; benzene at 20.4 - 50.3℃; Kinetics;

trimethylsilyl bromide (2857-97-8) + Hexamethylphosphorous triamide (1608-26-0) → N,N-Dimethyltrimethylsilylamine (2083-91-2) + Brom-bis-dimethylamino-phosphan (20502-36-7)

Conditions	Yield
Ambient temperature;

trimethylsilyl fluoride (420-56-4) + bis(dimethylamino)dimethylsilane (3768-58-9) + Dimethyl-N-dimethylamino-fluor-silan (661-62-1) → dimethyldifluorosilane (353-66-2) + N,N-Dimethyltrimethylsilylamine (2083-91-2)

Conditions	Yield
at 120℃; Equilibrium constant;

trimethylsilyl fluoride (420-56-4) + bis(dimethylamino)dimethylsilane (3768-58-9) → dimethyldifluorosilane (353-66-2) + N,N-Dimethyltrimethylsilylamine (2083-91-2) + Dimethyl-N-dimethylamino-fluor-silan (661-62-1)

Conditions	Yield
at 120℃; Equilibrium constant;

chloro-trimethyl-silane (75-77-4) + Tetrakis(dimethylamino)methan (10524-51-3) → N,N-Dimethyltrimethylsilylamine (2083-91-2) + N,N,N',N',N'',N''-hexamethylguanidinium chloride (30388-20-6)

Conditions	Yield
In toluene 0 deg C to r.t., overnight; Yield given;

chloro-trimethyl-silane (75-77-4) + N,N-dimethylammonium chloride (506-59-2) → N,N-Dimethyltrimethylsilylamine (2083-91-2)

Conditions	Yield
With triethylamine; sodium iodide In acetonitrile for 0.5h; Ambient temperature; Yield given;

B2F4(N(CH3)2Si(CH3)3) (134620-31-8) → N,N-Dimethyltrimethylsilylamine (2083-91-2) + diboron tetrafluoride (13965-73-6)

Conditions	Yield
In neat (no solvent) during heating of B2F4*NMe2SiMe3;

N,N-Dimethyltrimethylsilylamine (2083-91-2) + S-Trifluormethyldifluorosulfonium(IV) Hexafluoroarsenat (31842-51-0) → Bis(dimethylamino)(trifluormethyl)sulfonium-hexafluoroarsenat (129813-16-7)

Conditions	Yield
-80 deg C -> RT;	100%

N,N-Dimethyltrimethylsilylamine (2083-91-2) + ((E)-(2R,3S)-3-Hydroxy-2,4,6-trimethyl-hept-4-enyl)-triphenyl-phosphonium; iodide → Triphenyl-((E)-(2R,3S)-2,4,6-trimethyl-3-trimethylsilanyloxy-hept-4-enyl)-phosphonium; iodide (136152-11-9)

Conditions	Yield
In dichloromethane	100%

N,N-Dimethyltrimethylsilylamine (2083-91-2) + chlorodimethylarsenium trifluoromethanesulfonate (141103-54-0) → bis(dimethylamino)arsenium trifluoromethanesulfonate (141103-62-0)

Conditions	Yield
	100%

N,N-Dimethyltrimethylsilylamine (2083-91-2) + chlorodiethylarsenium trifluoromethanesulfonate (141103-56-2) → diethylaminodimethylaminoarsenium trifluoromethanesulfonate (141103-64-2)

Conditions	Yield
	100%

N,N-Dimethyltrimethylsilylamine (2083-91-2) + Phenyl vinyl ketone (768-03-6) → Dimethyl-((Z)-3-phenyl-3-trimethylsilanyloxy-allyl)-amine

Conditions	Yield
In diethyl ether for 15h; Ambient temperature;	100%

N,N-Dimethyltrimethylsilylamine (2083-91-2) + 4-[4-(2-iodo-benzyl)-piperazin-1-yl]-cyclohexanone (749913-59-5) → {4-[4-(2-iodo-benzyl)-piperazin-1-yl]-cyclohex-1-enyl}-dimethyl-amine (749913-61-9)

Conditions	Yield
With toluene-4-sulfonic acid	100%

N,N-Dimethyltrimethylsilylamine (2083-91-2) + 4-[4-(2,5-difluoro-benzyl)-piperidin-1-yl]-cyclohexanone (749913-60-8) → {4-[4-(2,5-difluoro-benzyl)-piperidin-1-yl]-cyclohex-1-enyl}-dimethyl-amine (749913-62-0)

Conditions	Yield
With toluene-4-sulfonic acid	100%

{bis(trimethylsilyl)amino}-t-butylchloroborane (89487-06-9) + N,N-Dimethyltrimethylsilylamine (2083-91-2) → (tert-butyl)[bis(trimethylsilyl)amino](dimethylamino)borane (89487-12-7)

Conditions	Yield
In neat (no solvent) byproducts: Me3SiCl; under N2, equimolar amt. of Me3SiNMe2 was added to stirred (Me3Si)2NB(C(CH3)3)Cl at 0°C, warmed to room temp., stirred overnight; elem. anal.;	100%

N,N-Dimethyltrimethylsilylamine (2083-91-2) + S-(Perfluorethyl)thiazyldifluorid (111615-97-5) → trimethylsilyl fluoride (420-56-4) + S-(Dimethylamino)-S-(perfluorethyl)thiazylfluorid (111615-99-7)

Conditions	Yield
for 72h; -30 deg C to RT;	A n/a B 99%

N,N-Dimethyltrimethylsilylamine (2083-91-2) → 2,4,6-tris(dimethylamino)borazene (7360-02-3)

Conditions	Yield
With 2,4,6-trichloroborazine In dichloromethane at 20℃;	99%

N,N-Dimethyltrimethylsilylamine (2083-91-2) + (R)-3-hydroxy-5-phenyl-pentanoic acid ethyl ester (182417-58-9) → (3R)-ethyl 5-phenyl-3-trimethylsilyloxy-pentanoate (465545-16-8)

Conditions	Yield
at 20℃; for 16h;	99%
for 16h;

bis(dimethylamino)chlorocarbenium bis(pentafluorethyl)phosphinate + N,N-Dimethyltrimethylsilylamine (2083-91-2) → hexamethylguanidinium bis(pentafluorethyl)phosphinate

Conditions	Yield
In chloroform at 20℃; for 1h;	99%

B,B',B''-trichloroborazine (933-18-6) + N,N-Dimethyltrimethylsilylamine (2083-91-2) → 2,4,6-tris(dimethylamino)borazene (7360-02-3)

Conditions	Yield
In dichloromethane (Ar or N2), ligand in CH2Cl2 added slowly at -78°C to borazine inCH2Cl2, warmed to room temp.; evapd.(vac.), crystd. twice (CH2Cl2);	99%

N,N-Dimethyltrimethylsilylamine (2083-91-2) + 5-chloro-5H-dibenzo[a,d]cycloheptene (18506-04-2) → (5-H-dibenzo[a,d]cyclohepten-5-yl)-dimethylamine (4889-29-6)

Conditions	Yield
In toluene Inert atmosphere;	99%

N,N-Dimethyltrimethylsilylamine (2083-91-2) + ((C5(CH3)5)Fe(C5H4))2BBr (1233850-01-5) → ((C5(CH3)5)Fe(C5H4))2BN(CH3)2 (1233850-03-7)

Conditions	Yield
In toluene (N2) Me3SiNMe2 was added at room temp. to soln. Fe complex in toluene and stirred for 1 h; volatiles were removed in vacuo; elem. anal.;	99%

Pyridine-3-sulfonyl chloride (16133-25-8) + N,N-Dimethyltrimethylsilylamine (2083-91-2) → N,N-Dimethyl-3-pyridinsulfonsaeureamid

Conditions	Yield
In acetonitrile for 1h; Reflux; Inert atmosphere;	99%

N,N-Dimethyltrimethylsilylamine (2083-91-2) + dabsyl chloride (56512-49-3) → 4-(4-(dimethylamino)diazenyl)-N,N-dimethylbenzenesulfonamide (72720-19-5)

Conditions	Yield
In acetonitrile for 1h; Reflux; Inert atmosphere;	99%

N,N-Dimethyltrimethylsilylamine (2083-91-2) + cyclopropanesulfonyl chloride (139631-62-2) → N,N-dimethylcyclopropanesulfonamide

Conditions	Yield
In acetonitrile for 1h; Reflux; Inert atmosphere;	99%

N,N-Dimethyltrimethylsilylamine (2083-91-2) + dansyl chloride (51278-33-2) → 5-(dimethylamino)-N,N-dimethylnaphthalene-2-sulfonamide (1467025-04-2)

Conditions	Yield
In acetonitrile for 1h; Reflux; Inert atmosphere;	99%

N,N-Dimethyltrimethylsilylamine (2083-91-2) + C50H38FeNO3S → C45H37FeN2

Conditions	Yield
With titanium tetrachloride In toluene at 55℃; for 17h;	99%

6-methoxy-3-pyridinecarboxaldehyde (65873-72-5) + N,N-Dimethyltrimethylsilylamine (2083-91-2) + 3-methoxy-1-iodobenzene (766-85-8) → 1-(3-methoxyphenyl)-1-(6-methoxypyridin-3-yl)-N,N-dimethylmethanamine

Conditions	Yield
Stage #1: 6-methoxy-3-pyridinecarboxaldehyde; N,N-Dimethyltrimethylsilylamine With t-butyldimethylsiyl triflate In 1,4-dioxane for 0.05h; Inert atmosphere; Glovebox; Stage #2: 3-methoxy-1-iodobenzene With nickel(II) bromide dimethoxyethane; 2,6-bis(pyrazole)pyridine; zinc In 1,4-dioxane at 50℃; for 24h; Inert atmosphere; Sealed tube;	99%

N,N-Dimethyltrimethylsilylamine (2083-91-2) + 2-chloro-1,4-dimethoxybenzene (2100-42-7) → 3,6-dimethoxy-2-(trimethylsilyl) N,N-dimethylbenzenamine

Conditions	Yield
With lithium di-1-admantylamide In diethyl ether; cyclohexane at 50℃; for 24h; Inert atmosphere;	99%

N,N-Dimethyltrimethylsilylamine (2083-91-2) + 2,3,4,6-tetra-O-benzyl-D-galactopyranose (6386-24-9) → trimethylsilyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside

Conditions	Yield
In dichloromethane at 20℃; for 0.5h; Inert atmosphere;	99%

N,N-Dimethyltrimethylsilylamine (2083-91-2) + C50H37FeNO3S → C45H36FeN2

Conditions	Yield
With titanium tetrachloride	99%

pyridine-4-carbaldehyde (872-85-5) + N,N-Dimethyltrimethylsilylamine (2083-91-2) → Hexamethyldisiloxane (107-46-0) + (bis-dimethylamino methyl)-4 pyridine (122713-43-3)

Conditions	Yield
With bromine; trimethylsilyl trifluoromethanesulfonate In tetrachloromethane for 48h; Ambient temperature;	A n/a B 98%

3-pyridinecarboxaldehyde (500-22-1) + N,N-Dimethyltrimethylsilylamine (2083-91-2) → Hexamethyldisiloxane (107-46-0) + (bis-dimethylamino methyl)-3 pyridine (122713-46-6)

Conditions	Yield
With bromine; trimethylsilyl trifluoromethanesulfonate In tetrachloromethane for 18h; Ambient temperature;	A n/a B 98%

furfural (98-01-1) + N,N-Dimethyltrimethylsilylamine (2083-91-2) → (bis-dimethylamino methyl)-2 furanne (33500-19-5) + Hexamethyldisiloxane (107-46-0)

Conditions	Yield
With bromine; trimethylsilyl trifluoromethanesulfonate In tetrachloromethane for 4h; Ambient temperature;	A 98% B n/a

N,N-Dimethyltrimethylsilylamine (2083-91-2) + methyl vinyl ketone (78-94-4) → Dimethyl-((Z)-3-trimethylsilanyloxy-but-2-enyl)-amine

Conditions	Yield
In diethyl ether for 15h; Ambient temperature;	98%

N,N-Dimethyltrimethylsilylamine (2083-91-2) + 1-(Phenylsulfonyl)-1,2,3,4-tetrahydro-2-phenyl-4-quinolone (124857-02-9) → 1-Benzenesulfonyl-2-phenyl-4-trimethylsilanyloxy-1,2-dihydro-quinoline

Conditions	Yield
With toluene-4-sulfonic acid at 80℃; for 5h;	98%

N,N-Dimethyltrimethylsilylamine (2083-91-2) + 1,3-bis(dibromoboryl)cymantrene (1010720-67-8) → Mn(CO)3C5H3(B(N(CH3)2)2)2 (1148032-18-1)

Conditions	Yield
In toluene (N2); dropwise addn. of a soln. of Si compd. in toluene to a soln. of Mncomplex in toluene at room temp., stirring overnight; evapn. in vac., cooling at -40°C for 12 h;	98%

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 124-40-3 dimethyl amine 
• 14629-67-5 benzylthiotrimethylsilane 
• 107427-35-0 N,N-dimethylphenylmethane sulfenamide 
• 91749-17-6 trimethylsilyl <(dimethylamino)methyl>methylcarbamate 
• 10524-51-3 Tetrakis(dimethylamino)methan 
• 16029-98-4 trimethylsilyl iodide 
• 127-19-5 N,N-dimethyl acetamide 
• 68-12-2 N,N-dimethyl-formamide 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 134620-31-8 B₂F₄(N(CH₃)2Si(CH₃)3) 
• 51-80-9 bis-(dimethylamino)methane 
• 333361-87-8 bis(trimethylsilyl) [2-(2-furyl)-1-(trimethylsilyloxycarbonyl)ethyl]phosphonite 
• 333364-16-2 bis(trimethylsilyl) 2-(2-furyl)ethylphosphonite 

Downstream Products

• 420-56-4 trimethylsilyl fluoride 
• 52629-40-0 2-Trimethylsilyloxy-benzaldehyd-oxim 
• 18406-06-9 2-Trimethylsilyloxy-benzylidenoxim-O-trimethylsilyl-ether 
• 32115-55-2 N,N-Dimethylcarbamidsaeure-trimethylsilylester 
• 54731-41-8 Cyclohexan-1,2-dion-bis-(-O-trimethylsilyl-oxim) 
• 7684-30-2 N,N-dimethyl-N'-phenylcarbamimidic chloride 
• 24380-79-8 S-phenyl-N,N-dimethylsulfenamide 
• 31677-16-4 C₈H₁₁Br₂N₂O₂PS 
• 31646-27-2 C₁₀H₁₇Br₂N₂O₂PSSi 
• 1077-47-0 Dimethylamino-trifluor-phenyl-phosphoran 
• 38458-16-1 C₁₂H₂₂N₂O₂S₂Si 
• 29120-66-9 Dimethylamino-diphenyldifluorphosphoran 
• 67950-84-9 N,N,N',N'-Tetramethyl-1,3-diphenyl-[1,3,2,4]diazadiphosphetidine-2,4-diamine 
• 30543-43-2 1,1,2-Trimethyl-3-phenyl-isourea 

Relevant articles and documents

Latent Nucleophilic Carbenes

Using DFT and ab initio calculations, we demonstrate that noncyclic formamidines can undergo thermal rearrangement into their isomeric aminocarbenes under rather mild conditions. We synthesized the silylformamidine, for which the lowest activation energy in this process was predicted. Experimental studies proved it to serve as a very reactive nucleophilic carbene. The reactions with acetylenes, benzenes, and trifluoromethane proceeded via insertion into sp, sp2, and spCH bonds. The carbene also reacted with the functional groups, such as CHO, COR, and CN at double or triple bonds, displaying high mobility of the trimethylsilyl group. The obtained silylformamidine can be considered as a latent nucleophilic carbene. It can be prepared in bulk quantities, stored, and used when the need arises. Calculation results predict similar behavior for some other silylated formamidines and related compounds.

Organic [...] compound

This method for producing an organic silyl amine compound (3) represented by general formula (3) is characterized in that ammonia is removed by reactive distillation when an organic disilazane compound (1) represented by general formula (1) is reacted with an alkyl amine represented by general formula (2). An organic silyl amine compound can be obtained by this production method with high productivity without producing a salt. (In the formulae, each of R1, R2 and R3 independently represents a linear or branched alkyl group having 1-7 carbon atoms, a cyclic alkyl group having 3-5 carbon atoms or a phenyl group; and each of R4 and R5 independently represents a hydrogen atom, a linear or branched alkyl group having 1-5 carbon atoms or a cyclic alkyl group having 3-5 carbon atoms, provided that R4 and R5 are not hydrogen atoms at the same time.)

An Alumino-Mannich Reaction of Organoaluminum Reagents, Silylated Amines, and Aldehydes

A multi-component coupling using organoaluminum reagents, silylated amines, and aldehydes results in the formation of tertiary amines. Both alkenyl- and alkylaluminum reagents undergo reaction with iminium ion substrates for which the corresponding Petasis borono-Mannich reactions are unsuccessful.