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Cross dehydrogenative coupling (also known as CDC reaction), coined by Chao-Jun Li of 
The key to the CDC coupling is eliminating the need for substrate prefunctionalization. Therefore, the CDC reaction has the advantages of high efficiency,
McGill University
McGill University (french: link=no, Université McGill) is an English-language public research university located in Montreal, Quebec, Canada. Founded in 1821 by royal charter granted by King George IV,Frost, Stanley Brice. ''McGill Universit ...
, is a type of coupling reaction allowing the construction of a carbon–carbon bond
A carbon–carbon bond is a covalent bond between two carbon atoms. The most common form is the single bond: a bond composed of two electrons, one from each of the two atoms. The carbon–carbon single bond is a sigma bond and is formed b ...
or C-Heteroatom bond directly from C-H bonds in the presence of an oxidant
An oxidizing agent (also known as an oxidant, oxidizer, electron recipient, or electron acceptor) is a substance in a redox chemical reaction that gains or " accepts"/"receives" an electron from a (called the , , or ). In other words, an oxid ...
, leading to the thermodynamically unfavorable formal removal of a H2 molecule. As such, CDC are couplings belonging to the C-H activation strategy.
The key to the CDC coupling is eliminating the need for substrate prefunctionalization. Therefore, the CDC reaction has the advantages of high efficiency, Atom economy
Atom economy (atom efficiency/percentage) is the conversion efficiency of a chemical process in terms of all atoms involved and the desired products produced. The simplest definition was introduced by Barry Trost in 1991 and is equal to the ratio ...
and environmental friendliness. Such reactions can be achieved or activated by transition-metal catalysis or oxidation reaction (e.g. benzoquinone, peroxide
In chemistry, peroxides are a group of compounds with the structure , where R = any element. The group in a peroxide is called the peroxide group or peroxo group. The nomenclature is somewhat variable.
The most common peroxide is hydrogen p ...
s, O2, hypervalent iodine
Iodane generally refers to any organic derivative of iodine. Without modifier, ''iodane'' is the systematic name for the parent hydride of iodine, HI. Thus, any organoiodine compound with general formula RI (e.g., iodomethane , or iodobenzene ) ...
), or by either photocatalysis or electrocatalysis. The mechanism and reactivity of the CDC reactions varies dramatically depending on the substrate. CDC reactions have been used to construct bonds between sp3-sp3, sp3-sp2, sp3-sp, sp2-sp2, sp2-sp and sp-sp C-H bonds. The synthesis and functionalization of various nitrogen, oxygen and sulfur-containing heterocycles have also been achieved via CDC.
See also
* C-H activation *Cross-coupling
In organic chemistry, a cross-coupling reaction is a reaction where two fragments are joined together with the aid of a metal catalyst. In one important reaction type, a main group organometallic compound of the type R-M (R = organic fragment, M = ...
*Atom economy
Atom economy (atom efficiency/percentage) is the conversion efficiency of a chemical process in terms of all atoms involved and the desired products produced. The simplest definition was introduced by Barry Trost in 1991 and is equal to the ratio ...
* Oxidative coupling
References
{{Reflist Coupling reactions Organometallic chemistry Carbon-carbon bond forming reactions Catalysis