Tris(trimethylsilyl)silane and visible-light irradiation: a new metal- and additive-free photochemical process for the synthesis of indoles and oxindoles

Silva, Gustavo Piva da; Ali, Akbar; Silva, Rodrigo César da; Jiang, Hao; Paixão, Márcio W.

doi:10.1039/c5cc06329a

Cited by 67 publications

(41 citation statements)

References 83 publications

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“…Notably, entry 6 indicates that the silyl radical is likely not generated via a silane-aryl halide energy-transfer complex as previously proposed. 17 …”

Section: Design Planmentioning

confidence: 99%

Silyl Radical Activation of Alkyl Halides in Metallaphotoredox Catalysis: A Unique Pathway for Cross-Electrophile Coupling

2016

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A strategy for cross-electrophile coupling has been developed via the merger of photoredox and transition metal catalysis. In this report, we demonstrate the use of commercially available tris(trimethylsilyl)silane with metallaphotoredox catalysis to efficiently couple alkyl bromides with aryl or heteroaryl bromides in excellent yields. We hypothesize that a photocatalytically generated silyl radical species can perform halogen-atom abstraction to activate alkyl halides as nucleophilic cross-coupling partners. This protocol allows the use of mild yet robust conditions to construct Csp3–Csp2 bonds generically via a unique cross-coupling pathway.

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“…Notably, entry 6 indicates that the silyl radical is likely not generated via a silane-aryl halide energy-transfer complex as previously proposed. 17 …”

Section: Design Planmentioning

confidence: 99%

Silyl Radical Activation of Alkyl Halides in Metallaphotoredox Catalysis: A Unique Pathway for Cross-Electrophile Coupling

2016

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“…Not surprisingly, considerable effort is continually being made to develop new and efficient methods for their synthesis. Recently, the development of a useful method for the synthesis of indoles and oxindoles was described (da Silva et al, 2015). The protocol was based on a combination of tris(trimethylsilyl)silane, as the hydride source, and visible light to promote intramolecular reductive cyclization of suitable precursors.…”

Section: Chemical Contextmentioning

confidence: 99%

7-Methyl-5-[(4-methylbenzene)sulfonyl]-2H,5H-[1,3]dioxolo[4,5-f]indole: crystal structure and Hirshfeld analysis

et al. 2018

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In the title indole derivative, C17H15NO4S, the fused dioxolo-indole system is essentially planar [r.m.s. deviation of the 12 fitted atoms = 0.0249 Å] and is effectively perpendicular to the appended 4-tolyl ring, forming a dihedral angle of 89.95 (6)°. Overall, the molecule has the shape of the letter L. In the crystal, supramolecular layers in the ab plane are formed via weak 4-tolyl-C—H...π(C6-ring of indole) and S—O...π(1,3-dioxole) contacts. The aforementioned interactions along with interatomic H...H and H...O contacts are all shown to make significant contributions to the calculated Hirshfeld surfaces.

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“…Afterwards, UV‐Vis experiments suggested the formation of EDA (electron donor‐acceptor) complex between α‐keto acid and 2‐aminothiophenol by clearly shifting the absorption curve of 1 a + 2 a with reference to 1 a and 2 a (Figure ) . The formation of EDA complex was further justified by a change in the physical appearance of the solution of 1 a + 2 a (pale yellow) as compared to that of separate solutions of 1 a and 2 a (colourless) (Figure ).…”

Section: Resultsmentioning

confidence: 96%

“…In view of the results obtained from control experiments, UV‐Vis studies and literature precedence, the plausible mechanism is given in Scheme . First of all, EDA complex between 1 a and 2 a is formed.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Benzothiazoles via Photooxidative Decarboxylation of α‐Keto Acids

et al. 2020

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Herein, synthesis of benzothiazoles via decarboxylative cross-coupling between α-keto acids and 2aminothiophenols under blue LED irradiation without using any photocatalyst or metal at room temperature is described. The formation of benzothiazole is driven by the EDA (electron donor-acceptor) complex formed between α-keto acid and 2-aminothiophenol. This methodology gives easy access to 2-substituted and -unsubstituted benzothiazoles in moderate to good yields. α-Keto acids and 2-aminothiophenols bearing different functional groups were easily transformed under the given conditions.

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Tris(trimethylsilyl)silane and visible-light irradiation: a new metal- and additive-free photochemical process for the synthesis of indoles and oxindoles

Cited by 67 publications

References 83 publications

Silyl Radical Activation of Alkyl Halides in Metallaphotoredox Catalysis: A Unique Pathway for Cross-Electrophile Coupling

Silyl Radical Activation of Alkyl Halides in Metallaphotoredox Catalysis: A Unique Pathway for Cross-Electrophile Coupling

7-Methyl-5-[(4-methylbenzene)sulfonyl]-2H,5H-[1,3]dioxolo[4,5-f]indole: crystal structure and Hirshfeld analysis

Synthesis of Benzothiazoles via Photooxidative Decarboxylation of α‐Keto Acids

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