Handbook of Reagents for Organic Synthesis: Catalytic Oxidation Reagents

829 Pages·2013·134.15 MB·English

by  Philip L. Fuchs

General Abbreviations
Ac acetyl DIEA =DIPEA
acac acetylacetonate DIOP 2,3-O-isopropylidene-2,3-dihydroxy-1,4-
(cid:2)
AIBN 2,2-azobisisobutyronitrile bis-(diphenylphosphino)butane
Ar aryl DIPEA diisopropylethylamine
diphos =dppe
BBN borabicyclo[3.3.1]nonane DIPT diisopropyltartrate
BCME dis(chloromethyl)ether DMA dimethylacetamide
BHT butylated hydroxytoluene (2,6-di-t-butyl-p- DMAD dimethylacetylenedicarboxylate
cresol) DMAP 4-(dimethylamino)pyridine
(cid:2) (cid:2)
BINAL-H 2,2-dihydroxy-1,1-binaphthyl-lithium alu- DME 1,2-dimethoxyethane
minumhydride DMF dimethylformamide
(cid:2) (cid:2)
BINAP 2,2-bis(diphenylphosphino)-1,1- dmg dimethylglyoximato
binaphthyl DMPU N,N(cid:2)-dimethylpropyleneurea
(cid:2) (cid:2)
BINOL 1,1-bi-2,2-naphthol DMS dimethylsulfide
(cid:2)
bipy 2,2-bipyridyl DMSO dimethylsulfoxide
BMS borane–dimethylsulfide DMTSF dimethyl(methylthio)sulfonium
Bn benzyl tetrafluoroborate
Boc t-butoxycarbonyl dppb 1,4-bis(diphenylphosphino)butane
BOM benzyloxymethyl dppe 1,2-bis(diphenylphosphino)ethane
bp boilingpoint dppf 1,1(cid:2)-bis(diphenylphosphino)ferrocene
Bs brosyl(4-bromobenzenesulfonyl) dppp 1,3-bis(diphenylphosphino)propane
BSA N,O-bis(trimethylsilyl)acetamide DTBP di-t-butylperoxide
Bu n-butyl
Bz benzoyl EDA ethyldiazoacetate
EDC 1-ethyl-3-(3-dimethylaminopropyl)-
CAN cerium(IV)ammoniumnitrate carbodiimide
Cbz benzyloxycarbonyl EDCI =EDC
(cid:2)
CDI N,N-carbonyldiimidazole ee enantiomericexcess
CHIRAPHOS 2,3-bis(diphenylphosphino)butane EE 1-ethoxyethyl
Chx =Cy Et ethyl
cod cyclooctadiene ETSA ethyltrimethylsilylacetate
cot cyclooctatetraene EWG electronwithdrawinggroup
Cp cyclopentadienyl
CRA complexreducingagent
Fc ferrocenyl
CSA 10-camphorsulfonicacid
Fmoc 9-fluorenylmethoxycarbonyl
CSI chlorosulfonylisocyanate
fp flashpoint
Cy cyclohexyl
Hex n-hexyl
d density
HMDS hexamethyldisilazane
DABCO 1,4-diazabicyclo[2.2.2]octane
(cid:2) HMPA hexamethylphosphorictriamide
DAST N,N-diethylaminosulfurtrifluoride
HOBt l-hydroxybenzotriazole
dba dibenzylideneacetone
HOBT =HOBt
DBAD di-t-butylazodicarboxylate
HOSu N-hydroxysuccinimide
DBN 1,5-diazabicyclo[4.3.0]non-5-ene
DBU 1,8-diazabicyclo[5.4.0]undec-7-ene
(cid:2) Im imidazole(imidazolyl)
DCC N,N-dicyclohexylcarbodiimide
Ipc isopinocampheyl
DCME dichloromethylmethylether
IR infrared
DDO dimethyldioxirane
DDQ 2,3-dichloro-5,6-dicyano-1,4-benzoquinone
de diastereomericexcess KHDMS potassiumhexamethyldisilazide
DEAD diethylazodicarboxylate
DET diethyltartrate LAH lithiumaluminumhydride
DIBAL diisobutylaluminumhydride LD dosethatislethalto50%oftestsubjects
50
LDA lithiumdiisopropylamide PMDTA N,N,N(cid:2),N(cid:2)(cid:2),N(cid:2)(cid:2)-pentamethyldiethylene-
LDMAN lithium1-(dimethylamino)naphthalenide triamine
LHMDS =LiHMDS PPA polyphosphoricacid
LICA lithiumisopropylcyclohexylamide PPE polyphosphateester
LiHMDS lithiumhexamethyldisilazide PPTS pyridiniump-toluenesulfonate
LiTMP lithium2,2,6,6-tetramethylpiperidide Pr n-propyl
LTMP =LiTMP PTC phasetransfercatalyst/catalysis
LTA leadtetraacetate PTSA p-toluenesulfonicacid
lut lutidine py pyridine
RAMP (R)-1-amino-2-(methoxymethyl)pyrrolidine
m-CPBA m-chloroperbenzoicacid
rt roomtemperature
MA maleicanhydride
MAD methylaluminumbis(2,6-di-t-butyl-4-
salen bis(salicylidene)ethylenediamine
methylphenoxide)
SAMP (S)-1-amino-2-(methoxymethyl)pyrrolidine
MAT methylaluminumbis(2,4,6-tri-t-
SET singleelectrontransfer
butylphenoxide)
Sia siamyl(3-methyl-2-butyl)
Me methyl
MEK methylethylketone TASF tris(diethylamino)sulfonium
MEM (2-methoxyethoxy)methyl difluorotrimethylsilicate
MIC methylisocyanate TBAB tetrabutylammoniumbromide
MMPP magnesiummonoperoxyphthalate TBAF tetrabutylammoniumfluoride
MOM methoxymethyl TBAD =DBAD
MoOPH oxodiperoxomolybdenum(pyridine)- TBAI tetrabutylammoniumiodide
(hexamethylphosphorictriamide) TBAP tetrabutylammoniumperruthenate
mp meltingpoint TBDMS t-butyldimethylsilyl
MPM =PMB TBDPS t-butyldiphenylsilyl
Ms mesyl(methanesulfonyl) TBHP t-butylhydroperoxide
MS massspectrometry;molecularsieves TBS =TBDMS
MTBE methylt-butylether TCNE tetracyanoethylene
MTM methylthiomethyl TCNQ 7,7,8,8-tetracyanoquinodimethane
MVK methylvinylketone TEA triethylamine
TEBA triethylbenzylammoniumchloride
n refractiveindex TEBAC =TEBA
NaHDMS sodiumhexamethyldisilazide TEMPO 2,2,6,6-tetramethylpiperidinoxyl
Naph naphthyl TES triethylsilyl
NBA N-bromoacetamide Tf triflyl(trifluoromethanesulfonyl)
nbd norbornadiene(bicyclo[2.2.1]hepta- TFA trifluoroaceticacid
2,5-diene) TFAA trifluoroaceticanhydride
NBS N-bromosuccinimide THF tetrahydrofuran
NCS N-chlorosuccinimide THP tetrahydropyran;tetrahydropyranyl
NIS N-iodosuccinimide Thx thexyl(2,3-dimethyl-2-butyl)
NMO N-methylmorpholineN-oxide TIPS triisopropylsilyl
NMP N-methyl-2-pyrrolidinone TMANO trimethylamineN-oxide
NMR nuclearmagneticresonance TMEDA N,N,N(cid:2),N(cid:2)-tetramethylethylenediamine
NORPHOS bis(diphenylphosphino)bicyclo[2.2.1]-hept- TMG 1,1,3,3-tetramethylguanidine
5-ene TMS trimethylsilyl
Np =Naph Tol p-tolyl
TPAP tetrapropylammoniumperruthenate
TBHP t-butylhydroperoxide
PCC pyridiniumchlorochromate
TPP tetraphenylporphyrin
PDC pyridiniumdichromate
Tr trityl(triphenylmethyl)
Pent n-pentyl
Ts tosyl(p-toluenesulfonyl)
Ph phenyl
TTN thallium(III)nitrate
phen 1,10-phenanthroline
Phth phthaloyl
UHP urea–hydrogenperoxidecomplex
Piv pivaloyl
PMB p-methoxybenzyl Z =Cbz
Handbook of Reagents
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Handbook of Reagents
for Organic Synthesis
Reagents for Heteroarene Functionalization
Editedby
André B. Charette
UniversitédeMontréal,Montréal,QC,Canada
Thiseditionfirstpublished2015
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Handbookofreagentsfororganicsynthesis:reagentsforheteroarenefunctionalization/editedby
AndréB.Charette,UniversitédeMontréal,Montréal,QC,Canada.
pagescm
Includesindexes.
ISBN978-1-118-72659-4(cloth)
1. Organiccompounds–Synthesis. 2. Heterocyclicchemistry. 3. Chemicaltestsandreagents.
I. Charette,A.B.(AndréB.),1961-editor. II. Title:Reagentsfororganicsynthesis.
QD262.H26742015
547’.2–dc23
2015020137
AcataloguerecordforthisbookisavailablefromtheBritishLibrary.
ISBN13:978-1-118-72659-4
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e-EROS Editorial Board
Editor-in-Chief
DavidCrich
InstitutdeChimiedesSubstancesNaturelles(ICSN),Gif-sur-Yvette,France
ExecutiveEditors
AndréB.Charette
UniversitédeMontréal,Montréal,QC,Canada
PhilipL.Fuchs
PurdueUniversity,WestLafayette,IN,USA
TomislavRovis
ColoradoStateUniversity,FortCollins,CO,USA
FoundingEditor
LeoA.Paquette
TheOhioStateUniversity,Columbus,OH,USA