4.7 Review

Synthesis of Seleno-Heterocycles via Electrophilic/Radical Cyclization of Alkyne Containing Heteroatoms

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 362, Issue 17, Pages 3485-3515

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202000490

Keywords

Seleno-heterocycles; alkyne heteroatoms; beta-selenosulfonation; electrophilic; radical cyclization; selenated alkynes; selenide alkenes; selenium-beta-lactam; carbapenem heterocycle

Funding

  1. JSPS KAKENHI [17550099]
  2. MEXT: Monbukagakusho
  3. Grants-in-Aid for Scientific Research [17550099] Funding Source: KAKEN

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containing heterocyclic scaffolds by virtue of their interesting reactivities and a broad range of applications in the medicinal and materials chemistry. This review involves the electrophilic/radical cyclization of alkynes containing heteroatoms which resulted into the novel Se-heterocycles. The synthesis of seleno-heterocyclesviadifferent nucleophiles includingO,N,S,Se,Te, andC-nucleophiles is exhaustively discussed. Also, one-pot electrophilic cyclization of 1,3-diynes and 1,3,5-triynes was described in details. Furthermore, the various mechanisms underlying the synthesis of selenium-beta-lactam, carbapenem heterocycle, bis- and tris-selenide alkene, beta-selenosulfonation and selenated alkynes were discussed. The Se-heterocycles reported in this review allow preparing these selenated compounds bearing the selenium moiety both on the rings (outside) and inside the ring (e. g. selenophenes). The review demonstrates the growing opportunities to construct selenium containing heterocycles from alkynes containing heteroatoms.

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