Organic letters

Carbon-Based Leaving Group in Substitution Reactions: Functionalization of sp3-Hybridized Quaternary and Tertiary Benzylic Carbon Centers

SJ Mahoney, T Lou, G Bondarenko, E Fillion

Index: Mahoney, Stuart J.; Lou, Tiantong; Bondarenko, Ganna; Fillion, Eric Organic Letters, 2012 , vol. 14, # 13 p. 3474 - 3477

Full Text: HTML

Citation Number: 14

Abstract

Lewis acid promoted substitution reactions employing Meldrum's acid and 5-methyl Meldrum's acid as carbon-based leaving groups are described which transform unstrained quaternary and tertiary benzylic Csp3–Csp3 bonds into Csp3–X bonds (X= C, H, N). Importantly, this reaction has a broad scope in terms of both suitable substrates and nucleophiles with good to excellent yields obtained (typically> 90%).

 Related Synthetic Route
N/A Structure

1381982-75-7

N/A

trimethylaluminum Structure

75-24-1

trimethylaluminum

~99%

Benzene,1,3-bis(1,1-dimethylethyl)- Structure

1014-60-4

Benzene,1,3-bis...

5-[1-(4-methoxyphenyl)-1-methylethyl]-2,2-dimethyl-1,3-dioxane-4,6-dione Structure

1098072-77-5

5-[1-(4-methoxy...

~81%

anisole, p-isopropyl- Structure

4132-48-3

anisole, p-isop...

4-Anisylmagnesium bromide Structure

13139-86-1

4-Anisylmagnesi...

~%

anisole, p-isopropyl- Structure

4132-48-3

anisole, p-isop...

N/A Structure

1381982-95-1

N/A

trimethylaluminum Structure

75-24-1

trimethylaluminum

~94%

1-chloro-4-[1-(4-chlorophenyl)ethyl]benzene Structure

3547-04-4

1-chloro-4-[1-(...

Benzene,1,1'-(chloromethylene)bis[4-chloro- Structure

782-08-1

Benzene,1,1'-(c...

~%

1-chloro-4-[1-(4-chlorophenyl)ethyl]benzene Structure

3547-04-4

1-chloro-4-[1-(...

2,2-DIMETHYL-5-(PHENYLMETHYLENE)-1,3-DIOXANE-4,6-DIONE Structure

1214-54-6

2,2-DIMETHYL-5-...

phenylmagnesium bromide Structure

100-58-3

phenylmagnesium...

~60%

5-benzhydryl-2,2-dimethyl-1,3-dioxane-4,6-dione Structure

3962-41-2

5-benzhydryl-2,...

Meldrumic acid Structure

2033-24-1

Meldrumic acid

~%

5-benzhydryl-2,2-dimethyl-1,3-dioxane-4,6-dione Structure

3962-41-2

5-benzhydryl-2,...

Benzaldehyde Structure

100-52-7

Benzaldehyde

~%

5-benzhydryl-2,2-dimethyl-1,3-dioxane-4,6-dione Structure

3962-41-2

5-benzhydryl-2,...

5-[1-(4-methoxyphenyl)-1-methylethyl]-2,2-dimethyl-1,3-dioxane-4,6-dione Structure

1098072-77-5

5-[1-(4-methoxy...

trimethylaluminum Structure

75-24-1

trimethylaluminum

~92%

4-TERT-BUTYLANISOLE Structure

5396-38-3

4-TERT-BUTYLANISOLE

N/A Structure

1266101-50-1

N/A

trimethylaluminum Structure

75-24-1

trimethylaluminum

~95%

Benzene,1-methoxy-4-(1-phenylethyl)- Structure

2605-18-7

Benzene,1-metho...

4-Methoxybenzaldehyde Structure

123-11-5

4-Methoxybenzal...

~%

Benzene,1-methoxy-4-(1-phenylethyl)- Structure

2605-18-7

Benzene,1-metho...

5-[(4-METHOXYPHENYL)METHYLENE]-2,2-DIMETHYL-1,3-DIOXANE-4,6-DIONE Structure

15795-54-7

5-[(4-METHOXYPH...

~%

Benzene,1-methoxy-4-(1-phenylethyl)- Structure

2605-18-7

Benzene,1-metho...

Trimethylsilyl cyanide Structure

7677-24-9

Trimethylsilyl ...

5-[1-(4-methoxyphenyl)-1-methylethyl]-2,2-dimethyl-1,3-dioxane-4,6-dione Structure

1098072-77-5

5-[1-(4-methoxy...

~99%

Benzeneacetonitrile,4-methoxy-a,a-dimethyl- Structure

5351-07-5

Benzeneacetonit...

4-Anisylmagnesium bromide Structure

13139-86-1

4-Anisylmagnesi...

~%

Benzeneacetonitrile,4-methoxy-a,a-dimethyl- Structure

5351-07-5

Benzeneacetonit...

5-benzhydryl-2,2,5-trimethyl-1,3-dioxane-4,6-dione Structure

87057-91-8

5-benzhydryl-2,...

trimethylaluminum Structure

75-24-1

trimethylaluminum

~94%

1,1-Diphenylethane Structure

612-00-0

1,1-Diphenylethane

4-Methoxybenzaldehyde Structure

123-11-5

4-Methoxybenzal...

~%

Benzene,1,1'-ethylidenebis[4-methoxy- Structure

10543-21-2

Benzene,1,1'-et...

5-[(4-METHOXYPHENYL)METHYLENE]-2,2-DIMETHYL-1,3-DIOXANE-4,6-DIONE Structure

15795-54-7

5-[(4-METHOXYPH...

~%

Benzene,1,1'-ethylidenebis[4-methoxy- Structure

10543-21-2

Benzene,1,1'-et...

trimethylaluminum Structure

75-24-1

trimethylaluminum

2,2-dimethyl-5-(1-phenylcyclohexyl)-1,3-dioxane-4,6-dione Structure

83485-31-8

2,2-dimethyl-5-...

~99%

Benzene,(1-methylcyclohexyl)- Structure

828-45-5

Benzene,(1-meth...


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