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Adam's Catalyst: PtO2

   

Adams reagent: Zn(CN)2,

   

AIBN: 2,2'-Azobisisobutyronitrile [movies of AIBN decomposition]

   

Albright-Goldman  oxidation reagent: DMSO-Ac2O compare with Swern oxidation DMSO-CF3COOCOCF3

 

Synthesis 1990, 857-870

  • Pfitzner-Moffatt Procedure (DMSO/Dicyclohexylcarbodiimide)
  • Swern Procedure (DMSO/Oxalyl Chloride or CF3COOCOCF3)
  • Onodera Procedure (DMSO/Phosphorus Pentoxide)
  • Parikh-Doering Procedure (DMSO/Pyridine-Sulfur Trioxide)
  • Corey-Kim Procedure (Dimethyl Sulfide/N-Chlorosuccinimide)
  • Liu Procedure (DMSO/Phenyl Dichlorophosphate)
 

(R) or (S)- Alpine Borane B-isopinocamphenyl-9-borabicyclo, [3, 3, 1] nonane

 

Click here to learn more.

 

Appel Halogenation reagent: (Ph3PCl)+CCl3-

  CBr4, CCl3COCl3,

Attenburrow's Oxide: MnO2

 

Click here to learn more.

 

Barluenga iodination reagent: I(Py)2BF4

 

Angew. Chem. Int. ed. 1998, 37, 3136

1,2-iodofunctionalization of olefins or cyclization of alkynyl sulfides.

9-BBN:

   

BINAP:2,2'-Bis (diphenylphosphino)-1,1'binaphththyl) BINOL: Bi-2,2'naphthol

   

BMDA: bromo magnesium diisopropylamide, compare with LDA, lithium diisopropylamide

Thermodynamically control the Aldol condensation.

BMS: BH3-Me2S borane dimethylsulfide

 

Click here to learn more.

 

Brederick's reagent:t-Butoxybis(dimethylamino)methane

   

n-Butyl tin hydride: tri-n-butylstannane: (n-Bu)3SnH

   

Burgess reagent: MeOCONSO2NEt3 (carbomethoxysulfamoyl) triethylammonium inner salt

   

CAN: Ce(NH4)2(NO3)6 Cerium ammonium nitrate, CAS: Ce(NH4)4(SO4)4 cerium ammonium sulfate

   

Catecholborane:

   

CBS reagent: 

 

Tetrahedron Letters 1996, 37, 1023

 
 

Lei Zhu, Org. Proc. Research & Development, 2003, 7, 285

 

Cbz_Cl or Z-Cl: Benzyl chloroformate.

   

CDI: Staab reagent

   

Comins triflating reagent:

  Triflate separation using Al2O3 neutral.

Corey-Chaykovsky reagent: sulfur ylide Trimethylsufoxonium iodide

   

Corey-Seebathch reagent:

   

Crown Ether: 12-Crown-4.

   

CSA:  Camphorsulfonic acid

   

DABCO: or TED

   

Dast:

   

Davis oxidizing reagent:

   

dba: Bis(dibenzylideneactone)

   

Dienes,

Brassard's diene:Chan's diene: Dane's diene: Danishefsky's diene:

Rawal's diene:

   

DBU:  DBN:

   

DCC:  EDCI  Steglich-Hassner direct esterification

   

DDO: Dimethyldioxirane

   

DDQ:

   

DEAD:  vs ADDP:

   

Dess-Martin reagent:

   

DIBAL: REDA:

   

DMAP:

   

DPPE: DPPP:

   

Ender's reagents (SAMP, and RAMP)

SAMP:              RAMP:

   

Eschenmoser's salt:

   

Evans Chiral Auxiliary: Oxazolidinone

   

Furukawa's cyclopropanation reagent: Et2Zn/CH2I2

   

Furukawa's reagent: DMAP/MsCl

   

Gingras reagent: n-Bu4N+(Ph3SnF2)-, tetrabutylammonium difluorotriphenylstannate.

   

Gold reagent: activate methylene or amine group.

   

Grieco Reagent TolSO3-PyrH+, Pyridinium p-toluenesulfonate (PPTS).

   

 

Grubbs olefin metathesis: Schrock reagent, Hermann reagent, Tebbe reagent, Nugent reagent.

   

HMPA (HMPT): DMPU:

   

HMTA:

   

HBTU: vs HATU: HOBT:Cl-HOBt, HCTU, TCTU,PyBOP, PyAOP

 

Chimica Oggi, June, 2003, 6-11. Click here to learn more.

Very useful in peptide synthesis and amide formation. They are  all peptide coupling reagents.The OBt active esters are ledd reactive than O-acylisourea, but are more stable and less prone to racemize.

Horner-Wadsworth-Emmons reagent: (RO)2POCH2COOR'

   

Hunig's Base: diiisopropylethylamine

   

IBX (o-Iodoxybenzoic acid): Compare with Dess-Martin reagent.

 

J. Am. Chem. Soc. 2000, 122, 7596

 

Jacobsen catalyst:

   

Jacques' reagent:

   

KAPA: Potassium 3-aminopropylamide

   

Keinan Silane reagent: Diiodosilane (DIS)

   

KHMDS: potassium hexamethyldisilazide, or potassium bis(trimethylsilyl)amide, LHMDS: litium bis(trimethylsilyl)amide, NaHMDS, sodium hexamethyldisilazide

   

L-Selectride LiBH(s-Bu)3 Litium tri-s-butylborohydride

   

Lawesson's reagent:  Belleau's reagent, a mild reagent, is that the methyl groups have been replaced to phenyls.

Davy's reagent:is much strong reagent than Lawesson's reagent.

 

Tetrahedron Letters 1996, 37, 9107

 

Lemieux-Johnson reagent: NaIO4/OsO4

   

Lindar's catalyst: Pd/CaCO3/PbO

   

Lombardo reagent: CH2Br2/TiCl4/Zn

   

LTMP: Lithium 2,2,6,6-tetramethylpiperidide

   

Luche reagent: NaBH4+CeCl3

   

Magic methyl: MeOTf., it is extremely strong methylation reagent to non reactive nitrogens.

   

Mander's reagent: NCCO2Me,  to making ester.

   

Martin Dehydrating reagent: Ph2S[OC(CF3)2Ph)2

   

Meldrum's Lactone:

   

Meyer's reagent:

   

NBS: N-bromosuccinimide, NCS: N-chlorosuddinimide,

   

NMO: N-methylmorpholine-N-oxide,

   

Noyori catalyst: BINAP Ru or Rh complex

   

Olofson reagent

Oppolzer Chiral Auxiliary: Compare with Davis reagent.

   

Oxone: 2KHSO5/KHSO4/K2SO4

   

Pallaadacycle:

   

Pearlmann's Catalyst: Pd(OH)2/C

   

PPA: Polyphosphoric acid or Eaton's reagent: P2O5/MeSO3H

   

Pearlman reagent: Pd(OH)2 on carbon and Adam's catalyst PtO2

   

PdCl2 charcoal and LiOH was heated to yield Pd(OH)2

   

Proton Sponge:

   

PTSA: tosic acid

   

Rieche reagent: Cl2CHOMe or Cl2CHOBu, TiCl4 catalyzed formylation on hindered aromatics.

   

Rozen Hypofluorite reagents: AcOF, MeOF, HOF/MeCN

   

Schlosser's Base: n-BuLi/t-BuOK

   

Schwartz reagent:Hydrozirconation, clould be followed by Michael addition etc.

   

Schwesinger P-4 base

   

Sharpless AD-mix-a & AD-mix-b: Ti(OR)4/(+) or (-) Diehtyl tartarate (DET) /t-BuO2H (TBHP)

   

Stetter reagents:

   

Stiles' reagent: MeOMgOCO2Me, methyl magnesium carbonate (MMC)

   

Still-Gennari reagent: (CF3CH2O)2POCH2COOR

   

Super hydride: Lithium triethylborohydride

   

TBAF: tetrabutylammonium fluoride

   

TEMPO:

   

Varvoglis hypervalent iodine reagents: PhI(OCOCF3)2, PhI(OAc)2 (IBDA),

   

Viehe reagent: Me2N+=CCl2Cl-

   

Vilsmeier reagent: Me2N+=CHClCl-

   

Wilkinson's catalyst: RhCl(PPh3)3

 

Lei Zhu, Org. Lett., 2003, 5 (9), 1587

 
 

J. Org. Chem. 1997, 62, 4601

 

Yamada's reagent, DEPC, diethyl phosphoryl cyanide

   

Common linker:

Two carbon linkers

 

Dibromoethane is very irritating.

 

Three carbon linkers

 

Also dibromopropane is irritating.

 

 


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