Phosphorus Chemistry II pp 217-252

Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 361) | Cite as

Carbon–Hydrogen to Carbon–Phosphorus Transformations

Chapter

Abstract

Literature published between 2008 and 2013 concerning the functionalization of carbon–hydrogen into carbon–phosphorus bonds is surveyed. The chapter is organized by reaction mechanism. The majority of methods still proceed via deprotonation of C–H into C–M (M=Li, Na, etc.) followed by reaction with a phosphorus electrophile P–X, where X is usually chlorine. A few examples of electrophilic aromatic substitution and related processes have also been reported, although this approach has not yet been developed significantly. Over the past 5 years a rapidly growing family of reactions includes transition metal “C–H activation” and formally related radical-based processes has been developed. The latter processes offer exciting prospects for the synthesis of organophosphorus compounds.

Keywords

C–H activation Metallation Phosphanyl Phosphinyl Phosphonyl Phosphorus electrophiles Radical reactions 

Abbreviations

Ac

Acetyl

Ar

Aryl

BIPHEP

2,2′-Bis(diphenylphosphino)-biphenyl

Bn

Benzyl

Boc

tert-Butoxycarbonyl

Boc2O

Di-tert-butyl dicarbonate

Bp

Boiling point

Bpy

2,2′-Bipyridyl

BQ

1,4-Benzoquinone

brsm

Based on recovered starting material

Bu

Butyl

Bz

Benzoyl

CAN

Ceric ammonium nitrate

cat

Catalyst

concd

Concentrated

Cy

Cyclohexyl

d

Day(s)

(DHQD)2PYR

Hydroquinidine-2,5-diphenyl-4,6-pyrimidinediyl diether

DMF

Dimethylformamide

DMSO

Dimethyl sulfoxide

DOPO

6H-Dibenzo[c, e][1,2]oxaphosphorine 6-oxide

dppe

Bis(diphenylphosphino)ethane

dppf

1,1′-Bis(diphenylphosphino)ferrocene

dppm

Bis(diphenylphosphino)methane

ee

Enantiomeric excess

equiv.

Equivalent(s)

Et

Ethyl

h

Hour(s)

i-Pr

Isopropyl

KHMDS

Potassium hexamethyldisilazide potassium bis(trimethylsilyl)amide

LDA

Lithium diisopropylamide

LHMDS

Lithium hexamethyldisilazide lithium bis(trimethylsilyl)amide

Me

Methyl

Mes

Mesityl 2,4,6-trimethylphenyl (not methanesulfonyl)

min

Minute(s)

mol

Mole(s)

MTBE

Methyl tert-butyl ether

Nu

Nucleophile

Oct

n-Octyl

Ph

Phenyl

Pr

Propyl

py

Pyridine

rt

Room temperature

s

Second(s)

s-Bu

sec-Butyl

t-Bu

tert-Butyl

THF

Tetrahydrofuran

THP

Tetrahydropyran, tetrahydropyranyl

TMEDA

N,N,N′,N′-Tetramethylethylenediamine

TMS

Trimethylsilyl

Tol

4-Methylphenyl

Tr

Triphenylmethyl (trityl)

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Copyright information

© Springer-Verlag Berlin Heidelberg 2014

Authors and Affiliations

  1. 1.Department of ChemistryTexas Christian UniversityFort WorthUSA

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