Chan-Evans-Lam Coupling
The Chan-Evans-Lam coupling, also known as the Chan-Lam coupling, is a type of cross-coupling reaction that occurs between an aryl boronic acid and an alcohol or an amine. This reaction is catalyzed by copper complexes and can be conducted in air at room temperature[1][9].
The Chan-Evans-Lam coupling is named after Dominic Chan and Patrick Lam, who were among the first to develop this copper-catalyzed reaction[1]. It is a cost-effective method for generating carbon-carbon and carbon-heteroatom bonds using first-row transition metals, traditionally copper(II) salts, under mild conditions[12].
The reaction is particularly useful in the synthesis of various carbon-heteroatom or carbon-carbon bonds, making it a promising method in organic synthesis[3][6]. For example, the Chan-Lam coupling has been used to synthesize biologically active compounds. In one instance, a pyrrole was coupled with an aryl boronic acid to yield a product with a 93% yield[1].
Despite its advantages, the Chan-Evans-Lam coupling can also lead to side reactions such as deboration to yield benzene and oxidation or coupling with water to yield phenols or diphenyl ethers[7].
In comparison to other coupling reactions, such as the Buchwald-Hartwig coupling which relies on the use of palladium, the Chan-Evans-Lam coupling is more accessible due to the use of copper, a cheaper and more abundant metal[1][9].
Citations:
[1] https://en.wikipedia.org/wiki/Chan%E2%80%93Lam_coupling
[2] https://www.degruyter.com/document/doi/10.1515/9783110608373-023/html
[3] https://onlinelibrary.wiley.com/doi/10.1002/adsc.202000495
[4] https://www.sciencedirect.com/topics/chemistry/chan-lam-coupling
[5] https://www.youtube.com/watch?v=lwGK0VUAHMg
[6] http://sioc-journal.cn/Jwk_yjhx/EN/10.6023/cjoc201702001
[7] https://pubs.acs.org/doi/10.1021/acscatal.8b01881
[8] https://www.youtube.com/watch?v=E_ZF4iX5SEY
[9] https://www.wikiwand.com/en/Chan-Lam_coupling
[10] https://pubs.acs.org/doi/10.1021/acs.chemrev.9b00491
[11] https://www.wikiwand.com/en/Chan%E2%80%93Lam_coupling
[12] https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10184775/