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Kang, H. Parham Cyclization. Encyclopedia. Available online: https://encyclopedia.pub/entry/60886 (accessed on 23 October 2026).
Kang H. Parham Cyclization. Encyclopedia. Available at: https://encyclopedia.pub/entry/60886. Accessed October 23, 2026.
Kang, Helena. "Parham Cyclization" Encyclopedia, https://encyclopedia.pub/entry/60886 (accessed October 23, 2026).
Kang, H. (2026, October 12). Parham Cyclization. In Encyclopedia. https://encyclopedia.pub/entry/60886
Kang, Helena. "Parham Cyclization." Encyclopedia. Web. 12 October, 2026.

Parham Cyclization

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Parham cyclization is an intramolecular reaction in which an aryllithium or heteroaryllithium species, generated by halogen–lithium exchange on an aryl or heteroaryl halide, attacks an electrophilic group tethered to the same molecule. Rapid exchange at low temperature creates the organolithium intermediate while limiting competing proton transfer or reaction with external electrophiles; intramolecular addition then forms a fused or bridged carbocycle or heterocycle [1]. Tethered aldehydes, ketones, esters, amides, nitriles, epoxides, and related electrophilic sites can define the bond-forming terminus, with the particular functional group determining the immediate cyclic product [2]. The transformation is distinguished from aryne cyclization because the aryl halide is converted into an aryllithium nucleophile rather than eliminated to an aryne. It also differs from directed ortho-lithiation: halogen–lithium exchange establishes the reactive carbon, and productive ring closure requires a suitably positioned internal electrophile.

Parham cyclization aryllithium halogen–lithium exchange intramolecular addition
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References

  1. William E. Parham; Charles K. Bradsher; Aromatic organolithium reagents bearing electrophilic groups. Preparation by halogen-lithium exchange. Accounts Chem. Res. 1982, 15, 300-305. [CrossRef]
  2. Jie Jack Li. Parham cyclization; Springer Nature: Durham, NC, United States, 2009; pp. 413-414. [CrossRef]
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Subjects: Chemistry, Organic
Contributor MDPI registered users' name will be linked to their SciProfiles pages. To register with us, please refer to https://encyclopedia.pub/register : Helena Kang
View Times: 3
Entry Collection: Organic Chemistry
Revision: 1 time (View History)
Update Date: 19 Oct 2026
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