Reagents
Benzyl Chloroformate (CbzCl)
CbzCl protects amines as benzyloxycarbonyl (Cbz) groups. The Cbz group is removed by hydrogenolysis (H₂/Pd) or strong acid.
Dess–Martin Periodinane (DMP)
DMP is a mild, selective oxidant for converting alcohols to aldehydes and ketones under neutral conditions. It is safer than chromium-based oxidants.
Di-tert-butyl Dicarbonate (Boc₂O)
Boc₂O protects amines as tert-butyl carbamates (Boc groups). The Boc group is removed by TFA or HCl in organic solvents.
Diethylaminosulfur Trifluoride (DAST)
DAST converts alcohols to alkyl fluorides and carbonyls to gem-difluorides. It is the most common fluorinating agent in organic synthesis.
Diisobutylaluminium Hydride (DIBAL-H)
DIBAL-H selectively reduces esters to aldehydes at low temperature and nitriles to aldehydes. It is a versatile reducing agent.
Fluorenylmethyloxycarbonyl Chloride (FmocCl)
FmocCl protects amines as Fmoc carbamates. The Fmoc group is removed by base (piperidine), making it ideal for solid-phase peptide synthesis.
Grignard Reagents (RMgX)
Grignard reagents are organomagnesium halides formed by reacting alkyl or aryl halides with magnesium metal. They are powerful nucleophiles and bases.
Lithium Aluminium Hydride (LiAlH₄)
LiAlH₄ is a powerful reducing agent that reduces esters, acids, amides, nitriles, and epoxides in addition to aldehydes and ketones.
Lithium Dialkylcuprates (Gilman Reagents)
Gilman reagents (R₂CuLi) are softer nucleophiles than Grignard or organolithium reagents, making them selective for 1,4-addition to enones.
meta-Chloroperoxybenzoic Acid (mCPBA)
mCPBA is the most common peracid for epoxidation of alkenes and Baeyer–Villiger oxidation of ketones. It is a stable, easy-to-handle oxidant.
N-Bromosuccinimide (NBS)
NBS is a source of electrophilic bromine used for allylic and benzylic bromination, and for bromination of electron-rich aromatics.
Organolithium Reagents (RLi)
Organolithium reagents are strong bases and nucleophiles. They are more reactive than Grignard reagents and must be handled at low temperatures.
Osmium Tetroxide (OsO₄)
OsO₄ dihydroxylates alkenes to give cis-1,2-diols. It is toxic and expensive but highly selective, often used catalytically with co-oxidants.
Pyridinium Chlorochromate (PCC)
PCC oxidizes primary alcohols to aldehydes and secondary alcohols to ketones without overoxidation. It is a milder alternative to Jones reagent.
Sodium Borohydride (NaBH₄)
NaBH₄ is a mild reducing agent that selectively reduces aldehydes and ketones to alcohols. It is safe, easy to handle, and compatible with many functional groups.
Swern Oxidation Reagent
The Swern oxidation uses DMSO and oxalyl chloride to oxidize alcohols under very mild conditions (-78°C). It is widely used in total synthesis.
tert-Butyldimethylsilyl Chloride (TBSCl)
TBSCl protects alcohols as silyl ethers. The TBDMS group is stable to many reaction conditions and removed by fluoride (TBAF) or acid.
Tetrakis(triphenylphosphine)palladium(0)
Pd(PPh₃)₄ is the most commonly used palladium catalyst for cross-coupling reactions including Suzuki, Heck, and Sonogashira couplings.