Iridium‐Catalyzed Reductive (3+2) Annulation of Lactams Enabling the Rapid Total Synthesis of (±)‐Eburnamonine DOI Creative Commons

Yasukazu Sugiyama,

Kento Yamada,

Daiki Kaneko

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 136(6)

Published: Dec. 13, 2023

Abstract A reductive (3+2) annulation of lactams through iridium‐catalyzed hydrosilylation and photoredox coupling with α‐bromoacetic acid was developed. The the lactam carbonyl group subsequent elimination provide a transient cyclic enamine, which undergoes in one‐pot process. developed conditions show high functional‐group tolerance N , O ‐acetals containing quaternary carbon center. resulting undergo variety acid‐mediated nucleophilic addition reactions via iminium ions to give substituted amines. sequence including successfully applied four‐step total synthesis (±)‐eburnamonine.

Language: Английский

Making Full Use of TMSCF3: Deoxygenative Trifluoromethylation/Silylation of Amides DOI
Yuxiao Wang, Shijun Li,

Feng Jiang

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(28), P. 19286 - 19294

Published: July 3, 2024

As one of the most powerful trifluoromethylation reagents, (trifluoromethyl)trimethylsilane (TMSCF3) has been widely used for synthesis fluorine-containing molecules. However, to best our knowledge, simultaneous incorporation both TMS- and CF3- groups this reagent onto same carbon products not realized. Herein, we report an unprecedented SmI2/Sm promoted deoxygenative difunctionalization amides with TMSCF3, in which silyl trifluoromethyl are incorporated into final product, yielding α-silyl-α-trifluoromethyl amines high efficiency. Notably, group could be further transformed other functional groups, providing a new method α-quaternary α-CF3-amines.

Language: Английский

Citations

12
Asymmetric Deoxygenative Functionalization of Secondary Amides with Vinylpyridines Enabled by a Triple Iridium-Photoredox-Chiral Phosphoric Acid System DOI

Xiyike Deng,

Feng Jiang,

Xiaoming Wang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(12), P. 2483 - 2488

Published: March 15, 2024

An enantioselective deoxygenative functionalization of secondary amides with vinylpridines is developed by merging relay iridium catalysis and cooperative photoredox-chiral Brønsted acid catalysis, affording a series valuable chiral amines in moderate to good yields enantioselectivities. The intriguing multiple catalytic system invoking triple-catalysis was found be the key success current reactions, which may stimulate further development methodologies for asymmetric transformations amides.

Language: Английский

Citations

4
A Novel Synergetic Effect and Photoactivation Lead to Very Effective UV–Visible–Infrared Light‐Driven Photothermocatalytic CO2 Reduction with CH4 on Ni/Ni‐Doped Al2O3 DOI
Youlin Chen, Huamin Cao, Yuanzhi Li

et al.

Solar RRL, Journal Year: 2023, Volume and Issue: 7(12)

Published: April 21, 2023

A nanocomposite of Ni nanoparticles (NPs) loaded on Ni‐doped Al 2 O 3 (Ni/Ni‐Al ) is prepared. Very effective photothermocatalytic dry reforming methane (DRM) acquired by Ni/Ni‐Al under focused UV–vis–IR illumination with a relatively low light intensity 80.7 kW m −2 . Under illumination, has high production rates H (, 72.62 mmol g −1 min and CO ( r , 88.29 as well large light‐to‐fuel efficiency η 28.0%. Compared reference catalyst NPs (Ni/Al ), the activity are enhanced its durability significantly improved due to coking rate being dramatically decreased 42.5 times. This attributed synergistic effect between Ni‐Al : active oxygen participates in oxidation carbon species one decisive steps for DRM, thus not only improving catalytic activity, but also promoting resistance. It found that plays heating role, substantially reduces activation energy resistance great acceleration upon (photoactivation).

Language: Английский

Citations

6
Iridium‐Catalyzed Reductive (3+2) Annulation of Lactams Enabling the Rapid Total Synthesis of (±)‐Eburnamonine DOI Creative Commons

Yasukazu Sugiyama,

Kento Yamada,

Daiki Kaneko

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 63(6)

Published: Dec. 13, 2023

A reductive (3+2) annulation of lactams through iridium-catalyzed hydrosilylation and photoredox coupling with α-bromoacetic acid was developed. The the lactam carbonyl group subsequent elimination provide a transient cyclic enamine, which undergoes in one-pot process. developed conditions show high functional-group tolerance N,O-acetals containing quaternary carbon center. resulting undergo variety acid-mediated nucleophilic addition reactions via iminium ions to give substituted amines. sequence including successfully applied four-step total synthesis (±)-eburnamonine.

Language: Английский

Citations

6
Radical Addition to Carbonyls (or C = X) Enabled by Visible Light Photoredox or Not DOI
Ke Zheng, Xiaohua Liu, Xiaoming Feng

et al.

Elsevier eBooks, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Language: Английский

Citations

1
Iridium‐Catalyzed Reductive (3+2) Annulation of Lactams Enabling the Rapid Total Synthesis of (±)‐Eburnamonine DOI Creative Commons

Yasukazu Sugiyama,

Kento Yamada,

Daiki Kaneko

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 136(6)

Published: Dec. 13, 2023

Abstract A reductive (3+2) annulation of lactams through iridium‐catalyzed hydrosilylation and photoredox coupling with α‐bromoacetic acid was developed. The the lactam carbonyl group subsequent elimination provide a transient cyclic enamine, which undergoes in one‐pot process. developed conditions show high functional‐group tolerance N , O ‐acetals containing quaternary carbon center. resulting undergo variety acid‐mediated nucleophilic addition reactions via iminium ions to give substituted amines. sequence including successfully applied four‐step total synthesis (±)‐eburnamonine.

Language: Английский

Citations

2