Functional Group Transformations – Back-up details

Alcohol to other Functional Groups

Dess-Martin Oxidation (Dess-Martin Periodinane, DMP)

Using PCC (Pyridinium Chlorochromate)

Using PDC (Pyridinium Dichromate)

Swern Oxidation (DMSO, Oxalyl chloride)

Pfitzner-Moffatt Oxidation (DMSO, DCC, acid)

Using MnO₂

Swern Oxidation variant (DMSO, TFAA)

Parikh–Doering oxidation (DMSO, py.SO₃)

Corey-Kim Oxidation (DMSO, NCS)

Using SOCl₂

Appel reaction (PPh₃, CCl₄)

Using Cyanuric chloride

Appel reaction (PPh₃, CBr₄)

Using HBr

Appel reaction (PPh₃, I₂, Im)

Using DAST

Using MsCl, base

Using Tosyl Cl, base

Using Tf₂O, base

Mitsunobu reaction

Using DPPA

Williamson synthesis

Mitsunobu reaction (ether formation)

Using Jones Reagent

Using NMO, TPAP (cat.)

Using NaClO, TEMPO (cat.)

Using Et₃SiH, TFA

Aldehyde/Ketone to other Functional Groups

NaBH₄ reduction

DIBAL-H reduction

Wittig and Wittig-Horner reactions

Tebbe Olefination (for terminal alkenes)

Schlosser Modification of Wittig reaction

Using DAST

Using Deoxofluor

Corey-Fuchs reaction, followed by n-BuLi (2 steps)

Wolff-Kishner reduction

Clemmensen reduction

Thioacetal, followed by reduction (2 steps)

Carboxylic acid to other Functional Groups

LAH or LiAlH₄ reduction

Borane.THF (BH₃.THF) reduction

Borane.Me₂S (BH₃.Me₂S) or BMS reduction

Acid activation, followed by NaBH₄ reduction

Using NaBH₄, I₂

Using DCC

Using EDCI, HOBt

Using EDCI, DMAP

Using T3P

Using HBTU

Using HATU

Using TBTU

Using NHS esters

Using BOP

Using py.BOP

Using Mukaiyama reagent

Using TSTU

acid chloride, followed by amine

acid anhydride, followed by amine

Esterification, followed by amine

Fischer Esterification

Using SOCl₂, followed by alcohol

Mitsunobu reaction (Ester formation)

Steglich Esterification (for t-butyl ester)

Using Me₂SO₄ (for methyl ester)

Using MeI, base (for methyl ester)

Ester to other Functional Groups

LAH or LiAlH₄ reduction

Using DIBAL-H

Using NaBH₄

Using LiBH₄

Ester hydrolysis under basic condition

Ester hydrolysis under acidic condition

Using DIBAL-H at -78^o C

Reduction to Alcohol, followed by oxidation to aldehyde (2 steps)

Nitrile to other Functional Groups

Using Basic condition

Using Acidic condition

Using LiAlH₄ reduction

Pd/C reduction

Raney Ni reduction

Using DIBAL-H

Using Urea-Hydrogen peroxide (UHP)

Pinner reaction (HCl, alcohol)

Amide to other Functional Groups

LAH or LiAlH₄ reduction

BH₃.THF (Borane THF) reduction

Using BH₃.Me₂S (BMS reduction)

Amide hydrolysis under basic condition

Amide hydrolysis under acidic condition

Hofmann rearrangement (for 1^o amide only)

Using POCl₃

Using SOCl₂

Using T3P

Using TFAA

Using Cyanuric chloride

Aromatic Substitution reactions (S_NAr)

S_NAr rean – F displacement

S_NAr rean – Cl displacement

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Haloalkane to other Functional Groups

Using CH₃COSH, K₂CO₃

(a) Phalimide reaction (b) Phthalimide cleavage (2 steps)

(a) NaN₃ (d) Reduction (Pd/C)

Using NaCN or KCN

Using Triethylphosphite, NaOH

(a) NaNO₂ (b) HCl

Alkene to other Functional Groups

(a) Ozonolysis (b) Reduction by NaBH₄ (2 steps)

(a) Hydroboration (b) Oxidation (2 steps)

Using OsO₄, NaIO₄

Using K₂OsO₄, NaIO₄

Using Pd/C, H₂

Using Pd/C, HCOONH₄

Using PtO₂, H₂

Using Zn, NH₄Cl (specific cases)

Using Raney Ni, NaBH₄

Using NaBH(OAc)₃ (specific cases)

Using LiAlH₄ (specific cases)

Asymmetric Reductions

(a) Bromination (b) Elimination (2 steps)

Using OsO₄, NMO

Using K₂OsO₄, NMO

Using mCPBA

Alkyne to other Functional Groups

Using Pd/C, H₂

Using Lindlar Catalyst

Using Br₂

Aromatic Electrophilic reactions

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Amine to other Functional Groups

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Epoxide to other Functional Groups

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Ether to other Functional Groups

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Aliphatic Substitution reactions (S_N1 and S_N2)

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Alkane to other Functional Groups

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Elimination reactions (E1 and E2)

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Acid chloride/Acid anhydride to other Functional Groups

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——– to other Functional Groups

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