Abbreviations xiiii-Pr isopropyl [Me 2 CH]
LDA lithium di-isopropylamide [LiN(i-Pr) 2 ] – hindered strong base
LiTMP lithium 2,2,6,6-tetramethylpiperidide [LiN(C(Me) 2 (CH 2 ) 3 C(Me) 2 ] – hindered non-nucleophilic
strong base
Me methyl [CH 3 ]
Ms methanesulfonyl (mesyl) [MeSO 2 ] – protecting group for azole nitrogen
NaHMDS sodium bis(trimethylsilyl)amide [sodium hexamethyldisilazide] [NaN(SiMe 3 ) 2 ] – hindered non-
nucleophilic strong base
NBS N-bromosuccinimide [C 4 H 4 BrNO 2 ] – brominating agent
NCS N-chlorosuccinimide [C 4 H 4 ClNO 2 ] – chlorinating agent
NMP N-methylpyrrolidin-2-one (1-methylpyrrolidin-2-one) [C 5 H 9 NO] – dipolar aprotic solvent
n-Bu normal butyl [CH 3 (CH 2 ) 3 ]
n-Pr normal propyl [CH 3 CH 2 CH 2 ]
Nu general designation for a negatively charged nucleophile
Ph phenyl [C 6 H 5 ]
PMB p-methoxybenzyl [4-MeOC 6 H 4 CH 2 ]
Pr see i-Pr and n-Pr
2-Py; 3-Py; 4-Py pyridin-2-yl; pyridin-3-yl; pyridin-4-yl [C 5 H 4 N]
R general designation for an alkyl group
o-Tol ortho-tolyl (2-methylphenyl) [C 7 H 7 ]
p-Tol para-tolyl (4-methylphenyl) [C 7 H 7 ]
rt room temperature (ca. 20 °C)
Selectfl uorTM 1-(chloromethyl)-4-fl uoro-1,4-diazoniabicyclo[2.2.2]octane tetrafl uoroborate – electrophilic
fl uorinating agent
SEM trimethylsilylethoxymethyl [Me 3 Si(CH 2 ) 2 OCH 2 ] – protecting group; removed with fl uoride
SES trimethylsilylethanesulfonyl [Me 3 Si(CH 2 ) 2 SO 2 ] – N-protecting group; removed with fl uoride
SPhos 2-dicyclohexylphosphino-2,6-dimethoxy-1,1-biphenyl – ligand for palladium(0)
syn on the same side (antonym of anti)
TBDMS t-butyldimethylsilyl [t-Bu(CH 3 ) 2 Si] – bulky silyl protecting group
t-Bu tertiary butyl [(CH 3 ) 3 C]
Tf trifl uoromethanesulfonyl [CF 3 SO 2 ], thus TfO trifl ate [CF 3 SO 3 ] – trifl ate is a good leaving
group
THF tetrahydrofuran – common ethereal solvent for dry reactions at low temperature
THP tetrahydropyran-2-yl [C 5 H 9 O] – protecting group; removed with aqueous acid
TIPS tri-isopropylsilyl [Si(i-Pr) 3 ] – protecting group for nitrogen or oxygen
TIPB 1,3,5-tri-iso-propylbenzene – inert high-boiling solvent
TMSCl trimethylsilyl chloride (chlorotrimethylsilane) [Me 3 SiCl] – O- and N-trimethylsilylating reagent
Tol same as p-Tol
TosMIC tosylmethyl isocyanide [TolSO 2 CH 2 NKC]
Ts p-toluenesulfonyl (tosyl) [p-TolSO 2 ] – Ts is a good protecting group for azole nitrogen and Ts can
be a leaving group (para-toluensulfi nate)
Tr trityl (triphenylmethyl) [Ph 3 C] – N-protecting group; removed with acid
TTF tetrathiafulvalene (C 6 H 4 S 4 )
X general designation for halogen (or in palladium(0) chemistry, sometimes OTf )