Synthesis of cyclopropyl silyl ethers and their facile ring opening by photoinduced electron transfer as key step in radical/radical cationic cascade reactions

Waske, Prashant A.; Mattay, Jochen

doi:10.1016/j.tet.2005.08.034

Cited by 21 publications

(13 citation statements)

References 33 publications

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“…The reactivity of silyloxycyclopropanes 81/85 under photoredox conditions was extensively studied by Mattey and co-workers under both UV and visible light conditions (Scheme 51). [94,95] Upon irradiation, the silyloxycyclopropanes 81/85 undergo oxidation to form the cationic radical which further facilitates the ring-opening to form β-keto radical. The β-keto radical intermediate cyclizes with alkyne or aromatic ring and a cascade reaction-chain termination leads to the formation of different carbocycles 82/83/84/85.…”

Section: Reaction Involving Cyclopropyl Alcohols and Derivativesmentioning

confidence: 99%

Visible‐Light‐Mediated Ring‐Opening Reactions of Cyclopropanes

et al. 2021

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Dedicated to Professor Ibrahim Ibnusaud for his outstanding contributions in the field of organic synthesisDue to the high reactivity of cyclopropanes, different methods have been developed for their stereo-and regio-controlled ring-opening reactions to achieve a variety of synthetically useful targets. The traditional methods for the ring-opening include thermolysis, use of oxidants, transition metals or radical precursors in which many of them encounter various difficulties. In the past several years, visible-light-mediated photoredox reactions received considerable attention for various organic transformations. Several methodologies have been developed in recent times for the visible-light-mediated ring-opening reactions of cyclopropanes. Considering the synthetic potential of this class of reactions, we provide a summary of various methodologies developed for the cyclopropane ring-opening reactions under visible-light photoredox catalysis.

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Section: Reaction Involving Cyclopropyl Alcohols and Derivativesmentioning

confidence: 99%

Visible‐Light‐Mediated Ring‐Opening Reactions of Cyclopropanes

et al. 2021

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“…Polycyclic compounds are also synthesized by ring expansion of 1-alkenyl-2-benzyl-1-cyclopentanol mediated by thallium trifluoroacetate [12] or ring opening of cyclopropyl silyl ethers upon oxidative photo-induced electron transfer. [13] So far, the most popular way to prepare tetralin derivatives is the [4 + 2] cycloaddition reaction between a dienophile and an in situ generated o-quinodimethane (oQDM). [14] There are several established methods for generating oQDMs including elimination of small molecules (SO 2 , CO 2 , N 2 , CO), [15] thermal benzocyclo- butene ring opening, [16] electrochemical and UV activation, [17] and reductive dehalogenation of a,a'-dihalo-1,2-dialkylbenzene halides.…”

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confidence: 99%

“…The pure, isolated, major isomer (34 % yield) was identified as the cis-isomer by comparison with literature data. [13] The trans-isomer was formed along with an unknown compound in an inseparable mixture. To the best of our knowledge, this methodology provides the first one-step access to compounds 6 and 7.…”

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confidence: 99%

Palladium‐Catalyzed Synthesis of Functional Tetralins via Benzylic Activation

2007

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“…Known compound 18 was prepared according to the literature procedure. 7 Experimental details will be reported in a full paper. In both cases, the residues were subjected to TLC separation to obtain unreacted 1 and products.…”

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confidence: 99%

“…Product 19 is a known compound. 7 Spectral data of products 4, 6, 15, 16, and 17 are described below.…”

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confidence: 99%