Alkynylation with Hypervalent Iodine Reagents

Topics in Current Chemistry
Jérôme Waser

Abstract

Alkynes are among the most versatile functional groups in organic synthesis. They are also frequently used in chemical biology and materials science. Whereas alkynes are traditionally added as nucleophiles into organic molecules, hypervalent iodine reagents offer a unique opportunity for the development of electrophilic alkyne synthons. Since 1985, alkynyliodonium salts have been intensively used for the alkynylation of nucleophiles, in particular soft carbon nucleophiles and heteroatoms. They have made an especially strong impact in the synthesis of highly useful ynamides. Nevertheless, their use has been limited by their instability. Since 2009, more stable ethynylbenziodoxol(on)e (EBX) reagents have been identified as superior electrophilic alkyne synthons in many transformations. They can be used for the alkynylation of acidic C-H bonds with bases or aromatic C-H bonds using transition metal catalysts. They were also highly successful for the functionalization of radicals or transition metal-catalyzed domino processes. Finally, they allowed the alkynylation of a further range of heteroatom nucleophiles, especially thiols, under exceptionally mild conditions. With these recent developments, hypervalent iodine reagents have d...Continue Reading

Citations

Oct 8, 2016·Journal of the American Chemical Society·Peng WangJin-Quan Yu
Jun 18, 2017·Journal of the American Chemical Society·Durga Prasad Hari, Jerome Waser
Feb 9, 2017·Chemistry : a European Journal·Gianpiero CeraLutz Ackermann
Jun 20, 2019·Organic & Biomolecular Chemistry·Rajnish BudhwanSandip Murarka
Jul 25, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ji Hoon LeeKi Bum Hong
Oct 28, 2019·Chemistry : a European Journal·Bin LiuGarret M Miyake
Jun 9, 2016·Angewandte Chemie·Marcus ReittiBerit Olofsson
Apr 7, 2021·The Journal of Organic Chemistry·Dhananjay YadavMaya Shankar Singh
May 13, 2021·Chemistry : a European Journal·Eliott Le DuJerome Waser
Apr 25, 2021·Angewandte Chemie·Igors SokolovsEdgars Suna
Sep 15, 2018·Journal of the American Chemical Society·Bin LiuGarret M Miyake
Apr 21, 2018·Organic Letters·Long LiuTieqiao Chen
Sep 23, 2021·Chemistry : a European Journal·János T CsenkiZoltán Novák

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