Fe‐Catalysed Coupling Reactions Between Alkynes and Alcohols

Abstract

In this review, we discussed about the synthetic developments in the field of Fecatalysis for the formation of -bonds through the coupling of alkynes and alcohols, for the period of 13 years (2008)(2009)(2010)(2011)(2012)(2013)(2014)(2015)(2016)(2017)(2018)(2019)(2020). These strategies fulfil important Green Chemistry principles, as they are highly atom economic (up to 100 %), no toxic by-products (only water), employs highly abundant and low toxic alcohols (no need for any pre-functionalization hence step economy) and cheaper Fe-catalysts. Having these advantages, one can predict that in the coming years a large number of fascinating new iron-catalyzed reactions will be developed for the organic synthesis. We hope that this review article will be highly useful for the synthetic community to design and develop new Fe-catalyzed coupling reactions and keeps the content in the right prospect.

Dehydrative alkynylation of 3-hydroxyisoindolinones with terminal alkynes for the synthesis of 3-alkynylated 3,3-disubstituted isoindolinones

“…At the outset, this seemingly incidental reaction may encounter several challenges such as the low reactivity of terminal alkynes, 16 c further alkyne hydration, 17 and the competition between 1,2- and 1,4-regioselectivity on the in situ formed ketimine intermediate. Nevertheless, we initiated our study by investigating different metal Lewis acids in the model reaction of 3-phenyl 3-hydroxyisoindolinone 1a with phenylacetylene 2a in ClCH 2 CH 2 Cl at 80 °C (Table 1).…”

“…1 Consequently, extensive efforts have been devoted to the development of efficient methods for the construction of organic molecules bearing C(sp)–C(sp 2 ) bonds or C(sp)–C(sp 3 ) bonds. 2 Among strategies for C(sp)–C(sp 3 ) bond formation, 2 e ,3–7 the alkynylation of electrophilic cationic N , O -acetals such as N -acyliminium ions represents one of the key reactions in forming propargylic amines. 2 e ,5 b ,8 However, in these reactions, there are only two examples using readily available terminal alkynes as alkynylation reagents (Scheme 1a).…”