Rhodium-catalyzed mild and selective C–H allylation of indolines and indoles with 4-vinyl-1,3-dioxolan-2-one: facile access to indolic scaffolds with an allylic alcohol moiety

Sharma, Satyasheel; Shin, Youngmi; Mishra, Neeraj Kumar; Park, Jihye; Han, Sim-Hee; Jeong, Taejoo; Oh, Yongguk; Lee, Youngil; Choi, Miji; Kim, In Su

doi:10.1016/j.tet.2015.02.052

Cited by 52 publications

(19 citation statements)

References 73 publications

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“…Va rious reports on amide-or ap yrimidyl-directed Rh IIIcatalyzed C1-functionalizations,s uch as heteroarylation, [226] alkylation, [227] cyanation, [221,229] allylation, [228] and alkenylation, [230] have been reported ( Table 2). Va rious reports on amide-or ap yrimidyl-directed Rh IIIcatalyzed C1-functionalizations,s uch as heteroarylation, [226] alkylation, [227] cyanation, [221,229] allylation, [228] and alkenylation, [230] have been reported ( Table 2).…”

Section: Angewandte Chemiementioning

confidence: 99%

“…In fact, by following this strategy,avariety of C7-functionalizations of indoline have been addressed in the past few years,i ncluding alkenylation, [231] alkylation, [227,232] allylation, [228,233] and cyanation [229] ( Table 3). In fact, by following this strategy,avariety of C7-functionalizations of indoline have been addressed in the past few years,i ncluding alkenylation, [231] alkylation, [227,232] allylation, [228,233] and cyanation [229] ( Table 3).…”

Section: Angewandte Chemiementioning

confidence: 99%

“…Similar to indole derivatives,c arbazole was also selectively functionalized by introducing ad irecting group on the NH moiety.The proximity of the C1ÀHand the incorporated directing group controls the selectivity of the reaction. Va rious reports on amide-or ap yrimidyl-directed Rh IIIcatalyzed C1-functionalizations,s uch as heteroarylation, [226] alkylation, [227] cyanation, [221,229] allylation, [228] and alkenylation, [230] have been reported ( Table 2).…”

Section: Indole and Its Derivativesmentioning

confidence: 99%

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Rhodium‐Catalyzed C(sp²)‐ or C(sp³)−H Bond Functionalization Assisted by Removable Directing Groups

2019

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In recent years, transition‐metal‐catalyzed C−H activation has become a key strategy in the field of organic synthesis. Rhodium complexes are widely used as catalysts in a variety of C−H functionalization reactions because of their high reactivity and selectivity. The availability of a number of rhodium complexes in various oxidation states enables diverse reaction patterns to be obtained. Regioselectivity, an important issue in C−H activation chemistry, can be accomplished by using a directing group to assist the reaction. However, to obtain the target functionalized compounds, it is also necessary to use a directing group that can be easily removed. A wide range of directed C−H functionalization reactions catalyzed by rhodium complexes have been reported to date. In this Review, we discuss Rh‐catalyzed C−H functionalization reactions that are aided by the use of a removable directing group such as phenol, amine, aldehyde, ketones, ester, acid, sulfonic acid, and N‐heteroaromatic derivatives.

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Section: Angewandte Chemiementioning

confidence: 99%

Section: Angewandte Chemiementioning

confidence: 99%

Section: Indole and Its Derivativesmentioning

confidence: 99%

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Rhodium‐Catalyzed C(sp²)‐ or C(sp³)−H Bond Functionalization Assisted by Removable Directing Groups

2019

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“…[61] Allylationw as also recently achieved at the C-2p osition of indoles,e xploiting pyrimidinea uxiliaries to direct the C À Ha ctivation. [62] …”

Section: Alkynylation Andalkenylationmentioning

confidence: 99%

Transition Metal‐Catalyzed CH Activation of Indoles

2015

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Thel ast decades have seen at remendous expanse in the applicationo fC À Ha ctivation of many different substrate classes,including the invaluable indole scaffold. Following the exciting emergence of C À Ha ctivation as am ulti-faceted platform for functionalization, av ersatile toolb ox has been developed for the preparation of structurally diverse indoles. This review article discussesr ecent advances and strategies for transitionm etal-catalyzed C À Ha ctivationofi ndoles.

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“…[5] In particular, VCCs have been frequently used in allylic substitu-tion chemistry [6] andC ÀHf unctionalization reactions. [7] Compared to vinyl epoxides,V CCs are not only more accessible, modulara nd easier to synthesize from readily available a-hydroxy ketones, but also their reactivity has provent ob ed ifferent in some cases. [8] Our group has focused on the functionalizationo fv inyl cyclic carbonates in palladium-catalyzed allylic substitution reactions with differentt ypes of nucleophiles.…”

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confidence: 99%

Formal Synthesis of Indolizidine and Quinolizidine Alkaloids from Vinyl Cyclic Carbonates

Cristòfol

Bohmer

Kleij

2019

Chemistry A European J

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Cyclic carbonates have long been considered relatively inert molecules acting as protecting groups in complex multistep synthetic routes. This study shows that a concise, yet modular synthesis of indolizidine and quinolizidine alkaloids can be developed from vinyl‐substituted cyclic carbonate (VCC) intermediates. Through a highly stereoselective palladium‐catalyzed allylic alkylation reaction, these alkaloid motifs can be assembled in four synthetic and only two column purification steps. The combined results help to further advance functionalized cyclic carbonates as useful and reactive intermediates in natural product synthesis.

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Rhodium-catalyzed mild and selective C–H allylation of indolines and indoles with 4-vinyl-1,3-dioxolan-2-one: facile access to indolic scaffolds with an allylic alcohol moiety

Cited by 52 publications

References 73 publications

Rhodium‐Catalyzed C(sp²)‐ or C(sp³)−H Bond Functionalization Assisted by Removable Directing Groups

Rhodium‐Catalyzed C(sp²)‐ or C(sp³)−H Bond Functionalization Assisted by Removable Directing Groups

Transition Metal‐Catalyzed CH Activation of Indoles

Formal Synthesis of Indolizidine and Quinolizidine Alkaloids from Vinyl Cyclic Carbonates

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Rhodium-catalyzed mild and selective C–H allylation of indolines and indoles with 4-vinyl-1,3-dioxolan-2-one: facile access to indolic scaffolds with an allylic alcohol moiety

Cited by 52 publications

References 73 publications

Rhodium‐Catalyzed C(sp2)‐ or C(sp3)−H Bond Functionalization Assisted by Removable Directing Groups

Rhodium‐Catalyzed C(sp2)‐ or C(sp3)−H Bond Functionalization Assisted by Removable Directing Groups

Transition Metal‐Catalyzed CH Activation of Indoles

Formal Synthesis of Indolizidine and Quinolizidine Alkaloids from Vinyl Cyclic Carbonates

Contact Info

Product

Resources

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Rhodium‐Catalyzed C(sp²)‐ or C(sp³)−H Bond Functionalization Assisted by Removable Directing Groups

Rhodium‐Catalyzed C(sp²)‐ or C(sp³)−H Bond Functionalization Assisted by Removable Directing Groups