Organic Synthesis Based on Name Reactions

In the present day, named chemical reactions play a vital role in organic synthesis. It continues to thrive in its ability to construct more diverse and complex chemical molecules.

The Lieben Haloform Reaction was the first-named reaction in organic synthesis, with its origin in 1822. Serullas found that iodine crystals dissolved in ethanol and alkali yielded a yellow precipitate which he named ‘hydroiodide of carbon’, called iodoform (CHI3) today.

In 1870, A. Lieben understood and studied the reaction of several carbonyl compounds with alkali and iodine and postulated rules that formulated the basis for the iodoform test. The iodoform test supported identifying the structure of several organic molecules Before spectroscopic methods became available for structural identification.

Till today, many new chemical reactions have been reported and named after the researchers who discovered them in recognition of their highly valuable contribution to synthetic organic chemistry. Yes, they deserve it!

What do we understand from Organic Synthesis Based on Name Reactions?

Name Reactions in Organic Synthesis are to honour the finders of groundbreaking chemical refinements or reactions of earlier known transformations.

  • It is done in such a way that several scientists get their names attached to a phenomenon or effect, a constant, an equation, etc.
  • In some cases, the researcher whose name is linked with the reaction wasn’t the first to discover that given reaction but instead managed to popularise it. We can also describe the reaction names and types, often by referring to structural features or initials.

For instance, carbon-carbon bond formation is vital in chemical synthesis, and name reactions exist that express and describe such transformations. In this particular field, the development of a procedure for utilising organomagnesium compounds by V.Grignard led to entirely new additional reactions that enlarged the scope of organic synthesis..

In a historical twist, Grignard wasn’t the first to use such reagents. However, he simplified the procedure by making the highly reactive reagent in situ.

The use of the related transformations got popularised, which had previously been tedious as the sensitive organomagnesium reagents required to be prepared and stored separately.

The modern-day term Grignard Reagents are used generally in conjunction with carbonyl compounds that supply alcohols and other substances with high yields. This process is now called the “Grignard reaction.” In a different instance, numerous C-C bond-forming reactions are facilitated by palladium catalysis.

This leads to better use of reagents and accessible conditions. One example is the synthesis of biaryl moieties. These are substructures that are frequently found in the interest compounds in medicinal chemicals.

To show how effective these reactions are, they are named after several variations of the reactions catalysed by palladium became popular within a couple of years of discovery, and even in the lifetime of the authors involved in the reactions, including (John Kenneth) (Makoto) Kumada, as well as J.K.) Stille and (Akira) Suzuki coupling. Other chemists who create specific modifications or variations, or hybrids, have their names incorporated in the Kumada-Tamao Corriu coupling.

Apart from the use of chemist’s names, there are also groundbreaking reactions that become identified by abbreviations of a descriptive name, like “RCM” (ring-closing metathesis) or INOC (intramolecular cyclisation of nitrile oxide).

We rarely use an individual’s name, such as the one who invented RCM (Robert Grubbs), about the reaction; however, you can recognise his contribution by naming the catalysts that use ruthenium.

We refer to “Grubbs catalyst,” “Grubbs catalyst”, or “2nd generation Grubbs catalyst”. Apart from names such as “RCM”, some frequently called reactions are named in honour of specific structural features of the product’s precursor.

Some examples include: “aldol reaction “aldol reaction” (“aldol” is an abbreviation for an aldehyde-containing compound with alcohol and aldehyde functions) and “pinacol rearrangement” or “pinacol rearrangement”.

Following are a few examples of Synthesis Based on Name Reactions

A

  • Acetoacetic Ester Condensation
  • Acyloin Condensation
  • Aldol Addition
  • Appel Reaction
  • Arndt-Eistert Synthesis
  • Azo Coupling

B

  • Baeyer-Villiger Oxidation
  • Balz-Schiemann Reaction
  • Barton Decarboxylation
  • Baylis-Hillman Reaction
  • Bischler-Napieralski Reaction
  • Blanc Reaction
  • Boronic Acid Mannich Reaction
  • Brook Rearrangement
  • Bucherer-Bergs Reaction

C

  • Cadiot-Chodkiewicz Coupling
  • CBS Reduction
  • Claisen Condensation
  • Clemmensen Reduction
  • Collins Reagent
  • Cope Rearrangement
  • Corey-Kim Oxidation
  • Corey-Suggs Reagent
  • Coumarin Synthesis
  • Cross Metathesis

D

  • Dakin Reaction
  • Darzens Reaction
  • De Kimpe Aziridine Synthesis
  • Dieckmann Condensation
  • 1,3-Dipolar Cycloaddition
  • Doebner Modification

E

  • Eglinton Reaction
  • Enyne Metathesis
  • Eschweiler-Clarke Reaction
  • Esterification

F

  • Favorskii Reaction
  • Fischer Esterification
  • Friedel-Crafts Alkylation
  • Fries Rearrangement
  • Fukuyama Reduction

G

  • Gabriel Synthesis
  • Glaser Coupling
  • Grubbs Reaction

H

  • Haloform Reaction
  • Hay Coupling
  • Hell-Volhard-Zelinsky Reaction
  • Horner-Wadsworth-Emmons Reaction
  • Huisgen Cycloaddition
  • Hydroboration

I

  • Ireland-Claisen Rearrangement
  • Iwanow Reaction (Reagent)

J

  • Jacobsen Epoxidation
  • Jocic Reaction
  • Jones Oxidation
  • Julia-Kocienski Olefination

K

  • Kabachnik-Fields Reaction
  • Knoevenagel Condensation
  • Kulinkovich Reaction
  • Kulinkovich-Szymoniak Reaction

L

  • Lawesson’s Reagent
  • Luche Reduction

M

  • Malonic Ester Synthesis
  • Markovnikov’s Rule
  • Meerwein-Ponndorf-Verley Reduction
  • Myers-Saito Cyclization
  • Michaelis-Arbuzov Reaction
  • Mukaiyama Aldol Addition

N

  • Nazarov Cyclization
  • Negishi Coupling
  • Nitroaldol Reaction
  • Nucleophilic Substitution (SN1 / SN2)

O

  • O’Donnell Amino Acid Synthesis
  • Olefin Metathesis
  • Overman Rearrangement
  • Ozonolysis

P

  • Paal-Knorr Furan Synthesis
  • Paal-Knorr Thiophene Synthesis
  • Paterno-Büchi Reaction
  • Pechmann Condensation
  • Prévost Reaction
  • Prilezhaev Reaction
  • Pschorr Reaction

Q

R

  • Ramberg-Bäcklund Reaction
  • Ring Closing Metathesis
  • Ritter Reaction
  • Rosenmund Reduction
  • Rubottom Oxidation

S

  • Sakurai Reaction
  • Saytzeff’s Rule
  • Schlosser Modification
  • Schotten-Baumann Reaction
  • Seyferth-Gilbert Homologation
  • Shapiro Reaction
  • Sharpless Dihydroxylation
  • Shi Epoxidation
  • Sonogashira Coupling
  • Staudinger Reaction
  • Staudinger Synthesis
  • Stetter Reaction
  • Strecker Synthesis
  • Swern Oxidation

T

  • Tamao-Kumada Oxidation
  • Tishchenko Reaction
  • Tsuji-Trost Reaction

U

  • Ugi Reaction
  • Upjohn Dihydroxylation

V

  • Van Leusen Oxazole Synthesis
  • Vicarious Nucleophilic Substitution

W

  • Wacker-Tsuji Oxidation
  • Wenker Synthesis
  • Williamson Synthesis
  • Wittig Reaction
  • Wolff-Kishner Reduction
  • Woodward cis-Hydroxylation
  • Wurtz Reaction

X

Y

  • Yamaguchi Esterification

Z

Why must you learn dozens or hundreds of name reactions?

As previously mentioned, Name reactions are utilised to describe revolutionary reactions or their associated mechanisms or the principles essential to know and keep straight.

Similar to how doctors must know the names of organs and geologists learn the name of mineral deposits, chemical chemists or students studying chemistry employ name reactions to organise their knowledge and talk regarding chemical reactions.

In laboratory discussions, people frequently use the term “name reaction” about the research they are undertaking or the chemical problems they are studying. Name reactions are an example of a shorthand term that does not need to elaborate on the features of a specific change of significance.

Anyone working in this industry is expected to be aware of the primary names of reactions. Name reactions allow the listener who has deep knowledge to think of the potential substrates, reaction conditions or mechanical information.

This makes the discussion more efficient. This is why name reactions are now part of the vocabulary used by organic chemical synthesis experts.

Conclusion

If you meet a fellow chemist in the conference or during an interview for a job, it is possible to determine the listener’s level of expertise and depth of knowledge and experience through a reference to an exotic name reaction.

This can indicate that the listener (or job applicant) is knowledgeable about specific areas of chemical research. This means that he could understand the details of the synthetic processes of the research described and might even come up with alternative ideas.

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