Ring-opening 1,3-arylboration of arylcyclopropanes mediated by BCl<sub>3</sub>

Kuboki, Yuichi; Arisawa, Mitsuhiro; Murai, Kenichi

doi:10.1039/d0ra08151e

Cited by 4 publications

(2 citation statements)

References 31 publications

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“…The earliest reports in this area can be traced back to the 1960s, when stoichiometric amounts of metal salts such as lead tetraacetate, thallium triacetate, or mercuric acetate were used by Ouellette and co-workers for the 1,3-diacetoxylation of aryl cyclopropanes. 3 Recently, other types of electrophiles, such as bromonium cation precursors, 4a hypervalent iodine reagents 4b or organoborane derivatives, 4c have also been employed in various 1,3-difunctionalization reactions (Scheme 1 ; top). Such reactions have been well summarized in a recent elegant review on aryl cyclopropanes.…”

Section: Introductionmentioning

confidence: 99%

Photoredox-Catalysis-Enabled Ring-Opening Functionalization of Aryl Cyclopropanes

Zhang

Feng

2022

Synlett

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Cyclopropanes have long been recognized as privileged synthons in organic synthesis to access 1,3-difunctionalized scaffolds. However, the synthetic potential of aryl cyclopropane, one of the most important subclasses of cyclopropanes, is far less explored. Recently, we uncovered a visible-light promoted strategy for the ring-opening functionalization of a series of aryl cyclopropanes through open-shell intermediates. By leveraging the activation of aryl radical cation derived from the oxidative single-electron-transfer (SET), C–C bond of cyclopropane is weakened and cleaves upon a regio- and stereoselective nucleophilic attack with exogenous nucleophiles to provide a benzyl radical that is readily elaborated to diverse functionalities.

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Section: Introductionmentioning

confidence: 99%

Photoredox-Catalysis-Enabled Ring-Opening Functionalization of Aryl Cyclopropanes

Zhang

Feng

2022

Synlett

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“…[5c] Although cyclopropanes do not have a multiple bond, the ring is an unsaturation equivalent, and the strained CÀ C bond could undergo a formal ring-opening 1,3hydroboration. [38] Unactivated cyclopropanes are the most common three-membered ring systems found in nature but methods for their selective ring-opening hydroboration are scarce. [39] In 1971, Rickborn and co-workers described the conversion of cyclopropanes with diborane (B 2 H 6 ) to afford alkylboranes at 100 °C, albeit with poor selectivity.…”

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confidence: 99%