by Thermo Fisher Scientific

1884 1886 1897 1909 1919 1954 1964 1974 1979

Sandmeyer reaction Knorr pyrrole synthesis Gattermann and Prilezhaev reaction Staudinger reaction Paterno-Büchi reaction Eschenmoser - Claisen Schwartz Suzuki cross-coupling
T. Sandmeyer L. Knorr Gattermann-Koch N.A. Prilezhaev H. Staudinger 1953 and J. Meyer E.P. di Sessa and G.H. Büchi rearrangement hydrozirconation reaction
Nobel
Prize Winner

Free radical reactions Generates an Heterocycle formation Used to formylation Electrophilic addition reactions Reduction reactions Pericyclic and photochemical reactions A. Eschenmoser D.W. Hart and A. Suzuki 2010
Nobel
Prize Winner

aryl halide from the corresponding aryl create substituted pyrroles through Reaction of an alkene with a peroxy Creates primary amines via the reaction between an Formation of oxetanes through the
diazonium salt using copper salts as reacting an α-amino-ketone L. Gattermann acid (often meta-chloroperoxyben- azide and phosphine, which form a reactive aza-ylide photochemical [2+2] cycloaddition of a
Pericyclic and photochemical reactions J. Schwartz Transition metal-catalyzed
Produces a γ,δ-unsaturated amide when an allylic Electrophilic addition reactions couplings
catalysts or reagents. and a compound containing an and J.A. Koch zoic acid (m-CPBA), due to its as an intermediate that is hydrolyzed spontaneously. carbonyl with an alkene. alcohol is heated with N,N-dimethylacetamide dimethyl Describes the use of the reagent Palladium catalyzed carbon-carbon
electron-withdrawing group Electrophilic aromatic substitution stability and good solubility in most acetal. bond formation where the coupling
N

:
PPh 3 N Zirconocene hydrochloride
:

:
1. NaNO2/HX e.g. an ester to a carbonyl group. reactions Creation of a formyl organic solvents) to form epoxides. :N PPh 3
: NN :
NH2 X N+ :
N- PPh 3 otherwise known as zirconocene partners are a boronic acid/ester or
2. CuX Ph N-
:
(aldehyde) functionality by treating Ph N - Ph
:
equivalent and an organohalide.
1968 chloride hydride, a metallocene

:
:
with a mixture of hydrogen cyanide - OH H
H : H used for various transformations of

: :
1946
H-OH N
:
(HCN) and hydrogen chloride (HCl)

: :
1887 1911 N Ph PPh 3 N
: :
N PPh Mislow-Evans rearrangement alkenes and alkynes.
1980
:
in the presence of a Lewis acid Ph Ph +PPh 3 O : Ph H
3
H

:
Reformatsky reaction
catalyst such as AlCl3.
Pictet-Spengler Jones oxidation K. Mislow and D. Evans
E.R.H. Jones and Pericyclic and photochemical reactions Noyori asymmetric
S. Reformatsky tetrahydroisoquinoline 1926 A general application for the preparation of
1978 hydrogenation
1882 Reactions involving carbonyl
compounds Condenses aldehydes or 1900 synthesis Meerwein–Ponndorf
colleagues
Oxidation
trans-allylic alcohols from allylic sulfoxides in a
R. Noyori
Nobel
Prize Winner

Hantzsch A. Pictet and T. Spengler 2,3-sigmatropic rearrangement. Swern oxidation 2001

Electrophilic addition reactions
ketones with α-halo esters using
Fries rearrangement –Verley reduction Used to convert primary
dihydropyridine metallic zinc to form β-hydroxy-esters.
Heterocycle formation alcohols into carboxylic (MeO)3P: D.Swern and co-workers The asymmetric hydrogenation of
H. Meerwein, O Ph

:
An important acid-catalyzed transformation
:
- Nucleophilic substitution reactions aldehydes, ketones and imines
K. Fries and colleagues S

:
acids or secondary alcohols PhS MeO H O
: :

:
: :

: :
synthesis W. Ponndorf and O

:
:
for the synthesis of tetrahydroisoquinolines into ketones using chromic R A mild oxidation that converts a primary or catalyzed by Ru(II)-BINAP and
Electrophilic aromatic R
A. Hantzsch from carbonyl compounds and R secondary alcohol to the corresponding related ruthenium complexes.
substitution reactions A. Verley acid (Jones Reagent). Me
Me
Me

1893 β-arylethylamines. OH aldehyde or ketone using oxalyl chloride,

:
:
Heterocycle formation Preperation of hydroxy aryl ketones Reduction reactions
dimethyl sulfoxide (DMSO) and an organic
1996
Produces R
through transformation of phenolic Hydrogenation which does not
1,4-dihydropyridines Pomeranz-Fritsch esters via Lewis acid catalysis. require the use of hazardous 1939 Me
base, such as triethylamine.
(DHPs), or “Hantzsch reaction Shi asymmetric
esters”, as isolable
C. Pomeranz and
pressurized H2 but utilizes
available, inexpensive, and
Meerwein 1973 1978 epoxidation
intermediates that can then
P. Fritsch 1901 1915 easy-to-handle hydrogen donor arylation Keck radical allylation Stille cross-coupling reaction Y. Shi
be oxidized to pyridines. molecules to carry out the H. Meerwein M. Kosugi and J. Grignon
R
Heterocycle formation Ullmann reaction Houben-Hoesch substrate hydrogenation. Free radical reactions J.K. Stille Electrophilic addition
Condensation of benzaldehydes or Free radical reactions Transition metal-catalyzed couplings reactions
F. Ullmann
O O R”OOC COOR”
R – CHO + 2
R’ OR”
+ NH3
R’ N
H
R’
arylketones with aminoacetalde- synthesis A powerful tool for the diverse
Used for the conversion of Palladium catalyzed carbon-carbon bond Synthesis of epoxides from
hyde acetals, it is used to Transition metal-catalyzed
couplings
K.Hoesch and J. Houben 1937 functionalization of alkenes through
addition of an aryl diazonium salt
aldehydes into homoallylic alcohols. formation via the coupling of an organotin various alkenes using a
synthesize isoquinolines. Electrophilic aromatic compound with a variety of organic fructose-derived organocatalyst
Traditionally the Ullmann Oppenauer (ArN2X) to an electron-poor alkene
substitution reactions usually supported by a metal salt. electrophiles. with Oxone as the primary
reaction refers to the synthesis
of symmetric biaryls via
This reaction is a type of oxidation Br Pd(PPh3)4
oxidant.
+ CH2 = CHSn(Ch2CH2CH2CH3)3
copper-catalyzed coupling at
Friedel-Crafts acylation with R.V. Oppenauer a stannane
hydrogen chloride and a Lewis acid Oxidation
THF
high temperatures
catalyst to prepare an aryl ketone Selective oxidation of CH = CH2
(200 °C).
from reaction of a nitrile with an secondary alcohols to + (CH3CH2CH2CH2)3SnBR
arene compound. ketones reaction takes place
in the presence of
[Al(i-PrO)3] in an excess of
acetone.

1870
Key named reactions in organic chemistry 2000

1950
1887 1941 Wittig reaction
Nazarov cyclization G. Wittig
Nobel
Prize Winner

1899
1979
Gabriel synthesis
N. Nazarov and G. Geissler
S. Gabriel Baeyer-Villiger Pericyclic and Reactions involving
Nucleophilic substitution photochemical reactions carbonyl compounds
reactions Traditionally using oxidation Used in the synthesis of Preparation of alkenes
potassium phthalimide transforms A. Baeyer 1905
Nobel
Prize Winner

1906 cyclopentenones from divinyl through reaction of an 1967

primary alkyl halides into primary
and V. Villiger ketones, it is a powerful tool aldehyde or ketone with a
amines.
Nucleophilic substitution Tishchenko 1919 to create 5-membered rings. triphenyl phosphonium
Mitsunobu reaction
reactions reaction Wohl-Ziegler bromination
ylide (often called a Wittig O. Mitsunobu 1983
1883
Generation of an ester from
a ketone or a lactone from a V. E. Tishchenko A. Wohl and +
reagent).
+ : + : -
Nucleophilic substitution
reactions 1978 Dess–Martin
O O Converts an alcohol into a oxidation
Nucleophilic substitution K. Ziegler 1963 Ph 3P Ph 3P : Ph 3P
Luche reduction

:
Nobel : :
cyclic ketone using
Prize Winner
H -: N(i-Pr) -

:
Fischer indole synthesis reactions
Me 2 Me
H Ph
Me Ph
variety of functional groups,
peroxyacids or peroxides. Free radical reactions Me Me Me H
J.L. Luche D.B. Dess and
E. Fischer 1913 such as an ester, using
Nobel
Prize Winner
Catalysed by aluminium Generates allylic and benzylic bromides Ph 3P - O Me H
1902 Reduction reactions A. Martin

:
:
alkoxides or sodium triphenylphosphine and an
and F. Jourdan through allylic or benzylic bromination of Me Ph The selective organic reduction of α, β-unsaturated
1894
Me Ph Oxidation
Heterocycle formation Generates
alkoxides generates Clemmensen reduction hydrocarbons using the reagent
Me H azodicarboxylate such as
ketones to allylic alcohols with sodium borohydride
the ester from the diethyl azodicarboxylate Oxidation of primary
aromatic heterocycle indole from a E.C. Clemmensen N-bromosuccinimide combined with (NaBH4) and lanthanide chlorides, such as cerium
(substituted) phenylhydrazine and an Knoevenagel corresponding aldehyde.
Reduction reactions a radical initiator. (DEAD) or diisopropyl
(III) chloride (CeCl3), in methanol or ethanol.
alcohols to aldehydes and
azodicarboxylate (DIAD). secondary alcohols to
aldehyde or ketone under acidic condensation Reduces aldehydes or ketones to 1939 1976
ketones via use of the
conditions. E. Knoevenagel alkanes in the presence of zinc Dess–Martin periodinane
amalgam and concentrated Hunsdiecker reaction
+
R”
(H+) R” (H+)
R”
Reactions involving
carbonyl compounds 1900 hydrochloric acid.
C. and H. Hunsdiecker 1970 Negishi cross-coupling (DMP) reagent.

HN O R’ HN +
H2N Often used to generate :
Zn Free radical reactions Heck reaction reaction
Grignard reaction 1917
N R’ N R’
NH2 O Zn O Zn
1958
Zn, HCI
.

1980
:
:

:
:

H
E. Negishi
Nobel
O
α,β-unsaturated ketones
: :
.
Ph Me Forms alkyl bromides via the T. Mizoroki and 2010
Prize Winner

V. Grignard Ph Me
Nobel
Ph Me
-H
through nucleophilic addition
+ Prize Winner
1912 decarboxylation of mercury or Transition metal-catalyzed couplings
Mannich reaction R.F. Heck
Nobel

Simmons–Smith Sharpless
Prize Winner
of an active hydrogen Reactions involving carbonyl H CI 2010
: :

HH silver salts of carboxylic acids by

:
Zn H CI The Negishi reaction is the coupling of organo
: :

:
- NH3 (H+)

HN
R”
HN
R”
NH2
R” compound to a carbonyl compounds Ph Me
H ZnCI
Ph Me
Ph Me C. Mannich treating with bromine. The alkyl cyclopropanation Transition metal-catalyzed zinc compounds catalysed by Pd or Ni catalyst. asymmetric
R’ H2N R’ R’ group followed by a Some important applications Reactions involving carbonyl bromide contains one fewer couplings Typically ArZnX + RX ---> Ar-R + ZnX2
H.E. Simmons Jr.
HN
dehydration reaction in which are the synthesis of alcohols, compounds Used frequently in the synthesis of epoxidation
a molecule of water is aldehydes or ketones, 1911 Formation of a β-amino-carbonyl
carbons than the carboxylic
acid. and R.D. Smith heterocyclic compounds the reaction K.B. Sharpless
Nobel
Prize Winner
2001
1877 eliminated. monocarboxylic acids, and
other organometallic or
Wolff–Kishner compound, also known as a
Mannich base, through amino
Electrophilic addition
reactions
of aryl halides or vinyl halides with
activated alkenes in the presence of 1974 and T. Katsuki
Oxidation
Friedel-Crafts acylation organometalloid compounds reduction alkylation of an acidic proton next 1937 Creation of a cyclopropane a Palladium-catalyst along with a
base for C-C bond formation. Rubottom oxidation Used to prepare
and alkylation reaction via organo magnesium N. Kishner to a carbonyl containing functional ring via an organozinc 2,3-epoxyalcohols from
intermediates. group by formaldehyde and a Overman rearrangement carbenoid that reacts with G.M. Rubottom, A.G. Brook
C. Friedel and J.M. Crafts and L. Wolff PdO
R primary and secondary
Electrophilic aromatic substitution Reduction reactions
primary or secondary amine or L. Overman an alkene (or alkyne). R – X + R’
base
R’
and A. Hassner allylic alcohols. The reaction is
R-X Mg R Mg X R Mg X ammonia.
.

Pericyclic and photochemical reactions -HX Oxidation catalyzed via a mixture of

reactions Converts carbonyl functionalities into
Acylation or alkylation of an aromatic alkanes. It is often used to remove a Generating allylic trichloroacetamides Used for the synthesis of α-hydroxy ketones through reaction of titanium tetra(isopropoxide)
R1 +
ring via reaction with an acyl or alkyl δ δ+ R1 H OH2 R1 carbonyl group after it has served its through an imidate intermediate from allylic silyl enol ethers with mCPBA, and subsequent rearrangement. and diethyl tartrate.
R MgX O R O– R OH H2O alcohols it has found application in
:

+
halide in the presence of a strong Lewis R1 R1 R1 synthetic purpose of activating an
MgX intermediate in a preceding step. asymmetric synthesis.
acid typically aluminium chloride. +

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