Tag: 135.1384

Intermolecular C-H Amidation of (Hetero)arenes to Produce Amides through Rhodium-Catalyzed Carbonylation of Nitrene Intermediates was written by Yuan, Si-Wen;Han, Hui;Li, Yan-Lin;Wu, Xueli;Bao, Xiaoguang;Gu, Zheng-Yang;Xia, Ji-Bao. And the article was included in Angewandte Chemie, International Edition in 2019.Recommanded Product: 7-Fluoroindole This article mentions the following:

Amide bond formation is one of the most important reactions in organic chem. because of the widespread presence of amides in pharmaceuticals and biol. active compounds Existing methods for amides synthesis are reaching their inherent limits. Described herein is a novel rhodium-catalyzed three-component reaction to synthesize amides from organic azides, carbon monoxide, and (hetero)arenes via nitrene-intermediates and direct C-H functionalization. Notably, the reaction proceeds in an intermol. fashion with N₂ as the only byproduct, and neither directing groups nor additives are required. The computational and mechanistic studies show that the amides are formed via a key Rh-nitrene intermediate. Thus, e.g., 1-methylindole + CO + TsN₃ 鈫?1-methyl-N-tosylindole-3-carboxamide (92%, 88% isolated) in presence of [Rh(cod)Cl]₂ in MeCN. In the experiment, the researchers used many compounds, for example, 7-Fluoroindole (cas: 387-44-0Recommanded Product: 7-Fluoroindole).

7-Fluoroindole (cas: 387-44-0) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Recommanded Product: 7-Fluoroindole

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

C2/C4 Regioselective Heteroarylation of Indoles by Tuning C-H Metalation Modes was written by Chen, Shuyou;Zhang, Min;Su, Rongchuan;Chen, Xingyu;Feng, Boya;Yang, Yudong;You, Jingsong. And the article was included in ACS Catalysis in 2019.Electric Literature of C8H6FN This article mentions the following:

The development of a rational strategy to achieve the complete regioselectivity and the capability to switch regioselectivity is an appealing, yet challenging, puzzle in transition-metal-catalyzed oxidative Ar-H/Ar-H cross-coupling. Disclosed herein is an iridium-catalyzed C2/C4 regioselective C-H heteroarylation of indoles with the help of a pivaloyl group at the C3 position. The judicious choice of the catalytic systems allows the C2-heteroarylation of indole via a concerted metalation-deprotonation (CMD) process and the C4-heteroarylation via a trimol. electrophilic substitution (S_E3) pathway. The oxidants Cu(OAc)₂路H₂O and Ag₂O are demonstrated to play a vital role in the C2/C4 regioselectivity. In this Article, a heteroaryl-Ir(III)-heteroaryl complex prior to reductive elimination is successfully isolated and characterized, which represents the first example of capturing the bis(hetero)aryl metallic intermediate in oxidative Ar-H/Ar-H cross-coupling. The regiodivergent heteroarylation of indoles developed herein provides an opportunity to rapidly assemble diverse C4- and C2-heteroarylated indoles. In the experiment, the researchers used many compounds, for example, 7-Fluoroindole (cas: 387-44-0Electric Literature of C8H6FN).

7-Fluoroindole (cas: 387-44-0) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Electric Literature of C8H6FN

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Bismuth nitrate-promoted disproportionative condensation of indoles with cyclohexanone: a new-type azafulvenium reactivity of indole was written by Kilic, H.;Bayindir, S.;Erdogan, E.;Agopcan Cinar, S.;Konuklar, F. A. S.;Bali, S. K.;Saracoglu, N.;Aviyente, V.. And the article was included in New Journal of Chemistry in 2017.Formula: C8H6FN This article mentions the following:

The bismuth nitrate-promoted disproportionative condensation of indoles such as 1H-indole, 2-methyl-1H-indole, 5-methoxy-1H-indole, 7-fluoro-1H-indole, etc. with cyclohexanone in one pot, to yield C3-cyclohexyl substituted indoles I (R¹ = R² = R⁵ = R⁷ = H; R¹ = R² = CH₃, R⁵ = R⁷ = H; R¹ = R² = R⁷ = H, R⁵ = OCH₃, etc.) and 1,3-di(1H-indol-3-yl)benzene derivatives II is reported for the first time. Using 3-methylindole with cyclopentanone, cyclohexanone, and cycloheptanone results in new and different synthetic pathways. The plausible reaction mechanisms are presented and supported with DFT (M06-2X/6-31+G(d,p)) calculations In the experiment, the researchers used many compounds, for example, 7-Fluoroindole (cas: 387-44-0Formula: C8H6FN).

7-Fluoroindole (cas: 387-44-0) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Formula: C8H6FN

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Palladium-catalyzed oxidative sulfenylation of indoles and related electron-rich heteroarenes with aryl boronic acids and elemental sulfur was written by Li, Jianxiao;Li, Chunsheng;Yang, Shaorong;An, Yanni;Wu, Wanqing;Jiang, Huanfeng. And the article was included in Journal of Organic Chemistry in 2016.Safety of 7-Fluoroindole This article mentions the following:

An efficient and convenient palladium-catalyzed C-H bond oxidative sulfenylation of 1-R²-2-R⁴-R³-indoles and 2-R⁴-6-R³-imidazo[1,2-a]pyridines with aryl boronic acids and elemental sulfur for the synthesis of 3-sulfenylindole derivatives I and II, resp. (R¹ = H, alkyl, MeO, halo, CN; R² = H, Me, PhCH₂; R³ = H, halo, alkyl, MeO, NO₂; R⁴ = H, Me, CO₂Et, Ph) is disclosed. This procedure provides a useful and direct approach for the assembly of a wide range of structurally diverse 3-sulfenylheteroarenes with moderate to excellent yields from simple and readily available starting materials. Moreover, this synthetic protocol is suitable for N-protected and unprotected indoles. Notably, the construction of two C-S bonds in one step was also achieved in this transformation. In the experiment, the researchers used many compounds, for example, 7-Fluoroindole (cas: 387-44-0Safety of 7-Fluoroindole).

7-Fluoroindole (cas: 387-44-0) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Safety of 7-Fluoroindole

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Intermolecular C-H Amidation of (Hetero)arenes to Produce Amides through Rhodium-Catalyzed Carbonylation of Nitrene Intermediates was written by Yuan, Si-Wen;Han, Hui;Li, Yan-Lin;Wu, Xueli;Bao, Xiaoguang;Gu, Zheng-Yang;Xia, Ji-Bao. And the article was included in Angewandte Chemie, International Edition in 2019.Recommanded Product: 7-Fluoroindole This article mentions the following:

Amide bond formation is one of the most important reactions in organic chem. because of the widespread presence of amides in pharmaceuticals and biol. active compounds Existing methods for amides synthesis are reaching their inherent limits. Described herein is a novel rhodium-catalyzed three-component reaction to synthesize amides from organic azides, carbon monoxide, and (hetero)arenes via nitrene-intermediates and direct C-H functionalization. Notably, the reaction proceeds in an intermol. fashion with N₂ as the only byproduct, and neither directing groups nor additives are required. The computational and mechanistic studies show that the amides are formed via a key Rh-nitrene intermediate. Thus, e.g., 1-methylindole + CO + TsN₃ → 1-methyl-N-tosylindole-3-carboxamide (92%, 88% isolated) in presence of [Rh(cod)Cl]₂ in MeCN. In the experiment, the researchers used many compounds, for example, 7-Fluoroindole (cas: 387-44-0Recommanded Product: 7-Fluoroindole).

7-Fluoroindole (cas: 387-44-0) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Recommanded Product: 7-Fluoroindole

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

C2/C4 Regioselective Heteroarylation of Indoles by Tuning C-H Metalation Modes was written by Chen, Shuyou;Zhang, Min;Su, Rongchuan;Chen, Xingyu;Feng, Boya;Yang, Yudong;You, Jingsong. And the article was included in ACS Catalysis in 2019.Electric Literature of C8H6FN This article mentions the following:

The development of a rational strategy to achieve the complete regioselectivity and the capability to switch regioselectivity is an appealing, yet challenging, puzzle in transition-metal-catalyzed oxidative Ar-H/Ar-H cross-coupling. Disclosed herein is an iridium-catalyzed C2/C4 regioselective C-H heteroarylation of indoles with the help of a pivaloyl group at the C3 position. The judicious choice of the catalytic systems allows the C2-heteroarylation of indole via a concerted metalation-deprotonation (CMD) process and the C4-heteroarylation via a trimol. electrophilic substitution (S_E3) pathway. The oxidants Cu(OAc)₂·H₂O and Ag₂O are demonstrated to play a vital role in the C2/C4 regioselectivity. In this Article, a heteroaryl-Ir(III)-heteroaryl complex prior to reductive elimination is successfully isolated and characterized, which represents the first example of capturing the bis(hetero)aryl metallic intermediate in oxidative Ar-H/Ar-H cross-coupling. The regiodivergent heteroarylation of indoles developed herein provides an opportunity to rapidly assemble diverse C4- and C2-heteroarylated indoles. In the experiment, the researchers used many compounds, for example, 7-Fluoroindole (cas: 387-44-0Electric Literature of C8H6FN).

7-Fluoroindole (cas: 387-44-0) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Electric Literature of C8H6FN

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Bismuth nitrate-promoted disproportionative condensation of indoles with cyclohexanone: a new-type azafulvenium reactivity of indole was written by Kilic, H.;Bayindir, S.;Erdogan, E.;Agopcan Cinar, S.;Konuklar, F. A. S.;Bali, S. K.;Saracoglu, N.;Aviyente, V.. And the article was included in New Journal of Chemistry in 2017.Formula: C8H6FN This article mentions the following:

The bismuth nitrate-promoted disproportionative condensation of indoles such as 1H-indole, 2-methyl-1H-indole, 5-methoxy-1H-indole, 7-fluoro-1H-indole, etc. with cyclohexanone in one pot, to yield C3-cyclohexyl substituted indoles I (R¹ = R² = R⁵ = R⁷ = H; R¹ = R² = CH₃, R⁵ = R⁷ = H; R¹ = R² = R⁷ = H, R⁵ = OCH₃, etc.) and 1,3-di(1H-indol-3-yl)benzene derivatives II is reported for the first time. Using 3-methylindole with cyclopentanone, cyclohexanone, and cycloheptanone results in new and different synthetic pathways. The plausible reaction mechanisms are presented and supported with DFT (M06-2X/6-31+G(d,p)) calculations In the experiment, the researchers used many compounds, for example, 7-Fluoroindole (cas: 387-44-0Formula: C8H6FN).

7-Fluoroindole (cas: 387-44-0) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Formula: C8H6FN

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Palladium-catalyzed oxidative sulfenylation of indoles and related electron-rich heteroarenes with aryl boronic acids and elemental sulfur was written by Li, Jianxiao;Li, Chunsheng;Yang, Shaorong;An, Yanni;Wu, Wanqing;Jiang, Huanfeng. And the article was included in Journal of Organic Chemistry in 2016.Safety of 7-Fluoroindole This article mentions the following:

An efficient and convenient palladium-catalyzed C-H bond oxidative sulfenylation of 1-R²-2-R⁴-R³-indoles and 2-R⁴-6-R³-imidazo[1,2-a]pyridines with aryl boronic acids and elemental sulfur for the synthesis of 3-sulfenylindole derivatives I and II, resp. (R¹ = H, alkyl, MeO, halo, CN; R² = H, Me, PhCH₂; R³ = H, halo, alkyl, MeO, NO₂; R⁴ = H, Me, CO₂Et, Ph) is disclosed. This procedure provides a useful and direct approach for the assembly of a wide range of structurally diverse 3-sulfenylheteroarenes with moderate to excellent yields from simple and readily available starting materials. Moreover, this synthetic protocol is suitable for N-protected and unprotected indoles. Notably, the construction of two C-S bonds in one step was also achieved in this transformation. In the experiment, the researchers used many compounds, for example, 7-Fluoroindole (cas: 387-44-0Safety of 7-Fluoroindole).

7-Fluoroindole (cas: 387-44-0) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Safety of 7-Fluoroindole

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles