Cover: Fiesers? Reagents for Organic Synthesis, VOLUME TWENTY NINE by Tse?Lok Ho

Fiesers’ Reagents for Organic Synthesis

VOLUME TWENTY NINE


Tse‐Lok Ho








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PREFACE

This volume covers mostly progress of synthetic organic methodologies for the period from the beginning of 2013 to mid‐2014. The major advances have been refinements of reagent applications and expansion of the scope.

The author thanks Jeffrey Ho, Dr. Sheng‐Ying Hsieh, Prof. Yun Li, and Dr. Geoff T’so for some indispensable literature help.

GENERAL ABBREVIATIONS

Ac
acetyl
acac
acetylacetonate
Ad
1‐adamantyl
AIBN
2,2’‐azobisisobutyronitrile
aq
aqueous
Ar
aryl
BARF
tetrakis[3,5‐bis(trifluoromethy)phenyl]borate
9‐BBN
9‐borabicyclo[3.3.1]nonane
BHT
butylated hydroxytoluene = (2,6‐di‐t‐butyl‐4‐methylphenol)
BINAP
2,2’‐bis(diphenylphosphino)‐1,1’‐binaphthyl
BINOL
1,1’‐binaphthalene‐2,2’‐diol
Bmim
N‐butyl‐N’‐methylimidazolium
Bn
benzyl
Boc
t‐butoxycarbonyl
bpy
2,2’‐bipyridyl
bpz
2,2’‐bipyrazine
BQ
1,4‐benzoquinone
Bs
benzenesulfonyl
Bu
n‐butyl
Bz
benzoyl
18‐c‐6
18‐crown‐6
c‐
cyclo‐
CAN
cerium(IV) ammonium nitrate
cap
caprolactamate
cat
catecholate
Cbz
benzyloxycarbonyl
cod
1,5‐cyclooctadiene
Cp
cyclopentadienyl
Cp*
1,2,3,4,5‐pentamethylcyclopentadienyl
CPME
cyclopentyl methyl ether
CSA
10‐camphorsulfonic acid
CuTC
copper(I) thienylcarboxylate
Cy
cyclohexyl
DABCO
1,4‐diazabicyclo[2.2.2]octane
DAST
(diethylamino)sulfur trifluoride
dba
dibenzylideneacetone
DBN
1,5‐diazabicyclo[4.3.0]non‐5‐ene
DBU
1,8‐diazabicyclo[5.4.0]undec‐7‐ene
DCC
1,3‐dicyclohecylcarbodiimide
DDQ
2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone
DEAD
diethyl azodicarboxylate
DIAD
diisopropyl azodicarboxylate
Dibal‐H
diisobutylaluminum hydride
DMA
N,N‐dimethylacetamide
DMAP
4‐dimethylaminopyridine
DMDO
dimethyldioxirane
DME
1,2‐dimethoxyethene
DMF
N,N‐dimethylformamide
DMPU
N,N’‐dimethylpropyleneurea
DMSO
dimethyl sulfoxide
DPM
dipivaloylmethane
DPPB
1,4‐bis(diphenylphosphino)butane
DPPE
1,2‐bis(diphenylphosphino)ethane
DPPF
1,1’‐bis(triphenylphosphino)ferrocene
DPPP
1,3‐bis(diphenylphosphino)propane
DTTB
4,4’‐di‐t‐butylbiphenyl
ee
enantiomer excess
Et
ethyl
Fc
ferrocenyl
Fmoc
9‐fluorenylmethoxycarbonyl
Fu
2‐furyl
HFIP
hexafluoroisopropanol
HMDS
hexamethyldisilazane
HMPA
hexamethylphosphoric amide
Hx
n‐hexyl
Ipc
isopinocampheyl
L
ligand
LAH
lithium aluminum hydride
LDA
lithium diisopropylamide
LED
light‐emitting diode
LHMDS
lithium hexamethyldisilazide
LiDBB
lithium 4,4’‐di‐t‐butylbiphenylide
LTMP
lithium 2,2,6,6‐tetramethylpiperidide
LN
lithium naphthaleneide
MCPBA
m‐chloroperbenzoic acid
Me
methyl
MEM
methoxyethoxymethyl
Mes
mesityl
MOM
methoxymethyl
Ms
methanesulfonyl
MS
molecular sieve
MTO
methyltrioxorhenium
NBS
N‐bromosuccinimide
NCS
N‐chlorosuccinimide
NHC
N‐heterocyclic carbene
NIS
N‐iodosuccinimide
NMO
N‐methylmorpholine N‐oxide
NMP
N‐methylpyrrolidone
Np
naphthyl
Ns
p‐nitrobenzenesulfonyl
Nu
nucleophile
Oc
n‐octyl
PEG
poly(ethylene glycol)
Ph
phenyl
phen
1,10‐phenanthroline
Pht
phthaloyl
pic
2‐picoline
pin
pinacolato
Piv
pivaloyl
PMB
p‐methoxybenzyl
PMHS
poly(methylhydrosiloxane)
PMP
p‐methoxyphenyl
Pr
n‐propyl
Py
pyridine
RaNi
Raney nickel
RCM
ring‐closing metathesis
RF
perfluoroalkyl
ROMP
ring opening methathesis polymerization
s
secondary
salen
N,N’‐ethenebis(salicylideneiminato)
SAMP
(S)‐1‐amino‐2‐methoxymethylpyrrolidine
SEM
2‐(trimethylsilyl)ethoxymethyl
SES
2‐[(trimethylsilyl)ethyl]sulfonyl
TBAF
tetrabutylammonium fluoride
TBDPS
t‐butyldiphenylsilyl
TBS
t‐butyldimethylsilyl
TEMPO
2,2,6,6‐tetramethylpiperidinoxy
TES
triethylsilyl
Tf
trifluoromethanesulfonyl
TFA
trifluoroacetic acid
TFAA
trifluoroacetic anhydride
THF
tetrahydrofuran
THP
tetrahydropyranyl
TIPS
triisopropylsilyl
TMEDA
N,N,N’,N’‐tetramethylethanediamine
TMS
trimethylsilyl
Tol
p‐tolyl
tpp
tetraphenylporphyrin
tpy
terpyridyl
Ts
p‐toluenesulfonyl
TSE
2‐(trimethylsilyl)ethyl
Z
benzyloxycarbonyl
Δ
heat
))))
ultrasound

REFERENCE ABBREVIATIONS

ACIE
Angew. Chem. Inter. Ed.
ASC
Adv. Synth. Catal.
CAJ
Chem. Asian J.
CC
Chem. Commun.
CEJ
Chem. Eur. J.
ChJC
Chinese J. Chem.
CL
Chem. Lett.
CO
ChemistryOpen
CS
Chem. Science
CSR
Chem. Soc. Rev.
EJOC
Eur. J. Org. Chem.
HCA
Helv. Chim. Acta
JACS
J. Am. Chem. Soc.
JCCS
J. Chinese Chem. Soc.
JOC
J. Org. Chem.
OBC
Org. Biomol. Chem.
OL
Org. Lett.
S
Synthesis
SL
Synlett
T
Tetrahed.
TL
Tetrahed. Lett.