Iodocyclization of Propargyl Alcohols: Highly Facile Approach to Hetero/Carbocyclic Iodides

Abstract

Iodocyclization of propargyl alcohols is an active area for the construction of hetero/carbocyclic iodides. Ambiphilic reactivity of propargyl alcohols made it more attractive to tune their reactivity towards the development of regioselective synthetic strategies. In general, iodocyclization reactions are atom and step economic, promoted by simple and readily available inexpensive electrophilic iodine reagents at ambient temperature. These compounds find potential applications in pharmaceutical and material sciences, because of the presence of a preinstalled reactive iodide functionality. Therefore, many researchers are actively involved in developing synthetic strategies towards iodocyclizations from propargyl alcohols for various applications. In this mini‐review, we emphasize the full list of synthetic endeavors made towards the “iodocyclization of propargyl alcohols, propargyl ethers and homopropargyl alcohols”.

From Propargylic Alcohols to Substituted Thiochromenes: gem-Disubstituent Effect in Intramolecular Alkyne Iodo/hydroarylation

“…Propargyl N -aryl amines and O -aryl ethers are versatile and precious building blocks. 1 The intramolecular alkyne arylation 2 of these building blocks provides straightforward access to relevant heterocycles such as hydroquinolines and chromenes, 3 , 4 without requiring a previous arene ortho functionalization. By contrast, this strategy involving C–H bond functionalization remains almost unexplored when applied to the synthesis of 2 H -thiocromenes from the related thioethers.…”

“…Propargyl N -aryl amines and O -aryl ethers are versatile and precious building blocks . The intramolecular alkyne arylation of these building blocks provides straightforward access to relevant heterocycles such as hydroquinolines and chromenes, , without requiring a previous arene ortho functionalization.…”

Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy

“…In the latter half of the 20th century, the halolactonizations of olefinic acids and amides, and the haloetherifications of olefinic alcohols were reported [ 4 , 5 , 6 , 7 ]. However, in the 21st century, there have been significant developments in halogen chemistry, as halogens have been determined to contribute to the control of high selectivities for the cyclization reactions [ 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 ]. In modern halogen chemistry, halogen-controlled reaction strategies that can contribute toward selective transformations have, thus, become an important issue and are of utmost interest in organic synthesis.…”

Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy

“…In the latter half of the 20 th century, the halolactonizations of olefinic acids and amides, and the haloetherifications of olefinic alcohols were frequently reported [4][5][6][7]. However, in the 21 st century, there have been significant developments in halogen chemistry, as halogens have been determined to contribute to the control of high selectivities for the cyclization reactions [8][9][10][11][12][13][14][15][16][17][18][19][20]. In modern halogen chemistry, halogen-controlled reaction strategies that can contribute toward selective transformations have thus become an important issue and are of interest in organic synthesis.…”