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Carbene Catalysts

Part of the Topics in Current Chemistry book series (TOPCURRCHEM,volume 291)

Abstract

The use of N-heterocyclic carbenes as catalysts for organic transformations has received increased attention in the past 10 years. A discussion of catalyst development and nucleophilic characteristics precedes a description of recent advancements and new reactions using N-heterocyclic carbenes in catalysis.

Keywords

  • Benzoin
  • Carbene
  • NHC
  • Nucleophilic Catalysis
  • Organocatalysis
  • Redox
  • Stetter
  • Transesterification
  • Umpolung

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Fig. 1
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Scheme 28
Scheme 29
Scheme 30
Scheme 31
Scheme 32
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Scheme 35
Scheme 36
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Scheme 39
Scheme 40
Scheme 41
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Scheme 45
Scheme 46
Scheme 47
Scheme 48
Scheme 49
Scheme 50
Scheme 51
Scheme 52
Scheme 53

Abbreviations

Ac:

acetyl

Ar:

aryl

BAL:

benzaldehyde lyase

BFD:

benzoylformate decarboxylase

Bmin:

butylmethylimidazolium

Bn:

benzyl

Boc:

tert-butoxycarbonyl

Bz:

benzoyl

Cy:

cyclohexyl

DABCO:

1,4-diazabicyclo[1.2.2]octane

DBU:

1,8-diazabicyclo[2.4.0]undec-7-ene

DCM:

dichloromethane

DIPEA:

diisopropylethylamine

DMF:

N,N-dimethylformamide

DMSO:

dimethylsulfoxide

Et:

ethyl

HOAt:

1-hydroxy-7-azabenzotriazole

i-Pr:

isopropyl

KHMDS:

potassium bis(trimethylsiyl)amide

KPi:

buffer potassium phosphate buffer

Me:

methyl

Mes:

mesityl (2,4,6-trimethylphenyl)

Ms methanesulfonyl (mesyl)MS:

molecular sieves

LiHMDS:

lithium bis(trimethylsilyl)amide

n-Bu:

normal-butyl

n-Hexnormal-hexyln-Pr:

normal-propyl

NHC:

N-heterocyclic carbene

PEMP:

pentamethylpiperidine

Ph:

phenyl

Pr:

propyl

TBS:

tert-butyldimethylsilyl

t-Bu:

tert-butyl

TES:

triethylsilyl

Tf:

trifluoromethanesulfonyl (triflyl)

ThDP:

thiamin diphosphate

THF:

tetrahydrofuran

TIPS:

triisopropylsilyl

TMS:

trimethylsilyl

Tol:

para-tolyl

Ts:

para-toluenesulfonyl (tosyl)

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Acknowledgements

The authors thank Jeffrey B. Johnson (Hope College), Javier Read de Alaniz, Mark S. Kerr and the Rovis group (CSU) for their careful reading of the manuscript. Support for our own efforts in this area has been provided by the National Science Foundation (CAREER) and the National Institutes of General Medical Sciences (GM72586). J.L.M. thanks the NIH for the Ruth L. Kirschtein NRSA pre-doctoral fellowship. T.R. thanks Johnson and Johnson, Eli Lilly, and Boehringer Ingelheim for unrestricted support, and the Monfort Family Foundation for a Monfort Professorship. T.R. is a fellow of the Alfred P. Sloan Foundation.

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Moore, J.L., Rovis, T. (2010). Carbene Catalysts. In: List, B. (eds) Asymmetric Organocatalysis. Topics in Current Chemistry, vol 291. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-02815-1_18

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