Progress in the Construction of Spirocyclohexadienones via Alkyne-Involving Dearomatization DOI Open Access
Peng Liu,

Fuming Zhong,

Lihao Liao

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 43(12), P. 4019 - 4019

Published: Jan. 1, 2023

Spirocyclohexadienones are not only widely present in bioactive molecules, but also act as key synthetic intermediates for the synthesis of natural products.Owing to great importance these compounds, their efficient has drawn considerable attention from chemists.In particular, there many reports about spirocyclohexadienone derivatives via alkyne-involving dearomatization past few years.The success reactions benefits reaction mode: activation alkyne π bond by radicals, electrophiles, or metal catalysts under conditions photocatalysis, electrocatalysis, chemical oxidation, and then subsequent process.The advances electron-deficient, electron-ordinary, electron-rich alkynes-participated phenolic realize construction recent five years systematically summarized.During discussion, used triggering ways subdivided.At last, prospects this field discussed.

Language: Английский

A general electron donor–acceptor complex enabled cascade cyclization of alkynes to access sulfur-containing heterocycles DOI
Wenchao Yang, Yu Sun, Xiaobo Bao

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(8), P. 3111 - 3116

Published: Jan. 1, 2023

A general visible light-promoted and electron–donor–acceptor complex-enabled cascade reaction of alkynes to produce functionalized sulfur-containing heterocycles under photocatalyst-, base-, oxidant- metal-free conditions was developed.

Language: Английский

Citations

30
Photo-induced spirocyclization of biaryl ynones with ammonium thiocyanate: access to thiocyanate-featured spiro[5,5]trienones DOI
Shiliu Chen,

Qinqin Yan,

Jie Fan

et al.

Green Chemistry, Journal Year: 2022, Volume and Issue: 25(1), P. 153 - 160

Published: Nov. 25, 2022

Photo-promoted cascade 6-exo-trig spirocyclization of biaryl ynones with NH 4 SCN was developed for the preparation various SCN-containing spiro[5,5]trienones.

Language: Английский

Citations

29
Thiols as Powerful Atom Transfer Catalyst: Opportunities in Photoredox‐Mediated Reactions DOI
Xiaobo Bao,

Wei Yu,

Guoli Wang

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(14), P. 2299 - 2309

Published: June 12, 2023

Abstract The employing visible light to drive organic transformations is the most promising choice meet needs for green synthesis, in which reactions promoted by may provide a more efficient and greener method. Currently, abundant methods activation functionalization of reaction substrates have relied on direct single‐electron transfer (SET) between excited photocatalyst substrates, these wonderful works were summarized docoumented many reviews. As complement above reactions, photoredox‐mediated atom (photocatalyst‐to‐HAT catalyst‐to‐substrates) generate radical species are showing an explosively growing trend. In this review, we highlight recent significant developments rapidly area, mainly focusing photoinduced base‐to‐substrates charge reactions.

Language: Английский

Citations

18
A Domino Dearomative ipso-Annulation/Desymmetrization Approach: Stereoselective Access to Tricyclic Alkaloid Skeletons DOI
Chada Raji Reddy,

A. Prasad,

Uprety Ajaykumar

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(23), P. 4904 - 4909

Published: June 5, 2024

Herein, we reveal an unprecedented domino annulation of

Language: Английский

Citations

9
EDA Complex-Enabled Annulation to Access CF2-Containing Tetralones and Quinazolinones Using Persulfates as Electron Donors DOI
Shupeng Zhang, Dawei Guo,

Mei-Ling Yang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10614 - 10623

Published: July 25, 2024

A photocatalyst-free and EDA complex-enabled radical cascade cyclization reaction of inactive alkenes with bromodifluoroacetamides was reported for the divergent synthesis fluorine-containing tetralones quinazolinones. In this transformation, persulfates as electron donors difluoro bromamide acceptors generate complex. This is a promising photochemical method advantages such mild conditions, simple operation, being metal-free, excellent functional group tolerance.

Language: Английский

Citations

7
Oxidative Cyclization of Aryl Ynones with NaNO2 for the Divergent Synthesis of NO2‐Containing Spiro[5.5]trienones, Indenones and Thioflavones DOI
Wenchao Yang,

Liu‐Yu Shen,

Junnan Li

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(21), P. 3651 - 3656

Published: Sept. 21, 2022

Abstract A K 2 S O 8 ‐promoted nitration/spirocyclization of biaryl ynones using inexpensive NaNO as nitro source has been described. This cascade reaction is triggered by nitration alkyne and followed 6‐exo‐trig spirocyclization, dearomatization, forming the NO ‐containing spiro[5.5]trienones in 63–85% yields. The present also provides a practical method for synthesis nitrated indenones thioflavones with 58–85% magnified image

Language: Английский

Citations

25
Trichloromethyl‐Radical‐Initiated Three‐Component Reaction of Alkenes with CHCl3 and Quinoxalinones DOI

Yechun Wu,

Jie Zhang,

Jin‐Tao Yu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(5), P. 687 - 692

Published: Feb. 8, 2023

Abstract An iron(II)‐catalyzed three‐component reaction was developed for the construction of trichloromethylated 3‐benzylquinoxalin‐2(1 H )‐ones. This conducted through trichloromethylation alkenes with quinoxalin‐2(1 )‐ones using commercially available chloroform as trichloromethyl radical source, which provided a convenient approach toward magnified image

Language: Английский

Citations

17
ipso-Cyclization of unactivated biaryl ynones leading to thio-functionalized spirocyclic enones DOI
Chada Raji Reddy,

Uprety Ajaykumar,

Amol D. Patil

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(31), P. 6379 - 6388

Published: Jan. 1, 2023

Dearomative ipso -annulation of unactivated biaryl ynones using AgSCN/AgSCF 3 as the radical source in presence CAN DMSO is disclosed.

Language: Английский

Citations

17
Divergent Construction of Thiochromanes and N-Arylbutanamides via Arylthiodifluoromethyl Radical-Triggered Cascade of Alkenes DOI
Yu Sun, Shupeng Zhang, Wenchao Yang

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(18), P. 13279 - 13290

Published: Aug. 31, 2023

A strategy utilizing silver-catalyzed oxidative decarboxylation radical cascade cyclization of arylthiodifluoroacetic acids with alkenes for the simple and efficient preparation difluoromethylated thiochromanes 2,2-disubstituted-N-arylbutanamides derivatives has been developed. This approach includes good functional group tolerance, easily accessible starting materials, operational simplicity.

Language: Английский

Citations

16
Nitro-Spirocyclization of Biaryl Ynones with tert-Butyl Nitrite: Access to NO2-Substituted Spiro[5,5]trienones DOI
Yang Li, Li‐Jun Li,

Changyou Guo

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(7), P. 4854 - 4862

Published: March 22, 2023

A metal/peroxide-free involved simple cascade 6-exo-trig spirocyclization of tert-butyl nitrite with biaryl ynones has been finished, which resulted in various NO2-modified spiro[5,5]trienones good regioselectivity/yields. variety scaled-up experiments, reduction/epoxidation operations, and mechanistic studies were performed to verify the merits process this radical system. Finally, structure spirocycles was confirmed by single-crystal X-ray diffraction.

Language: Английский

Citations

15