General and user-friendly protocol for the synthesis of functionalized aryl- and heteroaryl-cyclopropanes by Negishi cross-coupling reactions

Efficient Synthesis of Substituted 3‐Azabicyclo[3.1.0]hexan‐2‐ones from 2‐Iodocyclopropanecarboxamides Using a Copper‐Free Sonogashira Coupling

“…However, the majority of the reported examples involve cyclopropyl organometallic species as nucleophiles. [38][39][40][41][42][43] In 1996, Charette and Giroux made a major breakthrough and discovered that cycloA C H T U N G T R E N N U N G propyl iodides can be used as electrophilic partners in the Suzuki-Miyaura coupling with alkenylboronates, aryland heteroaryl-boronic acids. [44] Following this report, the Suzuki-Miyaura coupling between cyclopropyl iodides and cyclopropyl boronates was used to elaborate contiguous cycloA C H T U N G T R E N N U N G propane arrays, [45] whereas 2-iodocyclopropylboronates were identified as useful building blocks for the preparation of 1,2-disubstituted cyclopropanes.…”

Facile Synthesis of Polysubstituted Cyclopropanes Using a-Tosyloxyketones

“…To date, a number of traditional methods are available in the literature for cyclopropanation. Most common methods for synthesis of cyclopropane involve Negishi cross-coupling reactions [10], Simmon Smith reaction [11], transition metal-mediated carbene transfer from aliphatic diazo compounds to carbon-carbon double bonds [12], Michael initiated ring closure of ylides with electron-deficient olefins [13], etc. However, metal-free and economical synthetic methods are always in demand.…”

Regio- and stereoselective synthesis of tetrasubstituted allylic alcohols by three-component reaction of acetylenic sulfone, dialkylzinc, and aldehyde

“…Organozinc reagents are useful and versatile reagents for a variety of transformations in organic synthesis since they show high tolerance for a wide variety of functional groups [15][16][17][18][19]. Synthesis of di-or trisubstituted allylic alcohols by addition of alkenylzinc to aldehydes has been extensively studied and the alkenylzinc reagents are mainly generated in situ by reaction of dialkylzinc with alkenylboranes or alkenylzirconium, or by metal exchange of zinc chloride with alkenylmagnesium bromide and zinc bromide with alkenyllithium [20][21][22][23].…”