Indolsynthese durch Rhodium(III)‐katalysierte Hydrazin‐dirigierte C‐H‐Aktivierung: redoxneutral und spurlos durch N‐N‐Bindungsspaltung

Zhao, Dongbing; Shi, Zhuangzhi; Glorius, Frank

doi:10.1002/ange.201306098

Cited by 107 publications

(16 citation statements)

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“…[d] Yield of the mixture of regioisomers, in these cases, with 3-butyl indoles as the major products. and high-vacuum drying, the corresponding indoles (5)(6)(7)(8)(9)(10)(11)(12)(13) in the reported yields.…”

Section: General Informationmentioning

confidence: 79%

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Ruthenium‐Catalyzed Synthesis of Indoles from Anilines and Epoxides

Peña‐López

Neumann

Beller

2014

Chemistry A European J

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A general synthetic route to indoles from readily available anilines and epoxides by using ruthenium catalysis is described. This straightforward transformation allows a variety of indoles to be obtained in good yields by using [Ru3(CO)12]/1,1'-bis(diphenylphosphino)ferrocene as the catalytic system. Water and hydrogen are formed as the only stoichiometric by-products, making this process highly atom efficient.

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Section: General Informationmentioning

confidence: 79%

“…From our point of view, the ideal synthesis of indoles would be one that involves the direct connection of anilines with C2 fragments, such as alkenes or alkynes (Scheme 1 e). [13] Herein, we propose the use of epoxides, which are easily available from olefins, for the synthesis of indoles through metal-catalyzed dehydrogenation reactions.…”

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confidence: 99%

Ruthenium‐Catalyzed Synthesis of Indoles from Anilines and Epoxides

Peña‐López

Neumann

Beller

2014

Chemistry A European J

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“…[12] In sharp contrast, analogous additions of aryl C-H bonds across polar C5O, C5N, and C5C multiple bonds had seen considerably less progress before our reports on the pyridinyl-directed aryl C-H addition to aldehydes and 1,4-conjugate addition to 2-cyclohexenone. [13] However, it is both synthetically and mechanistically important to investigate the direct addition of Csp 2 -H bonds across polar C5O, C5N, and C5C bonds of a,b-unsaturated carbonyl compounds, because this not only gives mechanistically important information regarding the addition of Csp 2 -H bonds onto polar unsaturated bonds but also provides a greener alternative for the classical nucleophilic addition of organometallic reagents to polar unsaturated bonds.…”

Section: Introductionmentioning

confidence: 85%

Transition-Metal-Catalyzed Direct Addition of Aryl C-H Bonds to Unsaturated Electrophiles

Shi¹,

Han²,

Li³

2016

The Chemical Record

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The direct addition of Csp(2) -H bonds onto polar C=C, C=O, and C=N bonds is both synthetically and mechanistically important, because using aromatic C-H substrates in place of organometallic reagents provides a more direct and atom-economical alternative to many important compounds without the pre-generation of organometallic compounds from stoichiometric halides and the unavoidable generation of stoichiometric metal halide waste. In this account, we summarize our contributions to the transition-metal-catalyzed addition of aromatic C-H bonds to polar C=C, C=O, and C=N bonds via directing-group-assisted regiospecific reactions. These synthetic methods provide efficient access to benzylic alcohols, alkylbenzenes, 3-substituted phthalides, N-substituted phthalimides, N-aryl benzamides, and indene derivatives from commercially available reagents. It is worth noting that valuable heterocycles such as 3-substituted phthalides and N-substituted phthalimides can be obtained in one step by this approach.

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“…An acetate ligand of rhodacycle B dissociates to give the cationic complex C with assistance from HOAc; [22] this is followed by alkene coordination and insertion, thus affording the rhodacycle E (Scheme 6). The resulting seven-membered metallacycle presumably rearranges to the more stable six-membered coordinately saturated Rh species F by chelation with the Boc substituent, [24] which efficiently prevents competitive b-hydride elimination. [25] Complex F might undergo a nucleophilic addition to the N = N bond to form intermediate G, which is finally protonated by HOAc to yield the desired 1-aminoindoline.…”

Section: Methodsmentioning

confidence: 99%