A Computational Study on the Photochemical O–H Functionalization of Alcohols with Diazoacetates DOI
Chao Pei, René M. Koenigs

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(10), P. 6832 - 6837

Published: May 2, 2022

In this computational study, we provide a detailed analysis of the underlying reaction mechanism and show that singlet carbene is initially formed. Depending on pKA alcohol, can engage in direct protonation or enol formation to yield O-H functionalization product. On contrary, propargylic alcohols take up dual role form complex with intermediate leads facile cyclopropenation reactions.

Language: Английский

Visible-Light-Initiated Multicomponent Reactions of α-Diazoesters to Access Organophosphorus Compounds DOI

Chengming Qu,

Jindong Hao,

Hongyu Ding

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(19), P. 12921 - 12931

Published: Sept. 21, 2022

A simple visible-light-initiated strategy has been established for the construction of organophosphorus compounds via aerobic multicomponent reaction α-diazoesters, cyclic ethers, and P(O)H under air. number phosphonates phosphinates could be efficiently isolated in moderate to good yields without use photosensitizers metal reagents. This advantages mild condition, operation, eco-friendly energy, functional-group tolerance, gram-scale synthesis.

Language: Английский

Citations

16

Elemental sulfur as the “S” source: visible-light-mediated four-component reactions leading to thiocyanates DOI

Zhiwei Wang,

Ruisheng Liu,

Chengming Qu

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(13), P. 3565 - 3570

Published: Jan. 1, 2022

An eco-friendly and photocatalyst-free visible-light-promoted four-component reaction of α-diazoesters, elemental sulfur, cyclic ethers TMSCN leading to thiocyanates is described.

Language: Английский

Citations

15

Visible-light-mediated multi-component carbene transfer reactions of α-diazoesters to construct multisubstituted pyrazoles and 1,3-dicarbonyl derivatives DOI

Hongyu Ding,

Zhiwei Wang,

Chengming Qu

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(20), P. 5530 - 5535

Published: Jan. 1, 2022

A visible-light-promoted strategy has been developed for the assembly of multisubstituted pyrazoles and 1,3-dicarbonyl derivatives via a multi-component carbene transfer reaction α-diazoesters.

Language: Английский

Citations

15

Carbon-oxygen bond formation via visible-light-induced O–H insertion between acylsilanes and oximes DOI Creative Commons
Bao‐Gui Cai, Qian Li, Lei Li

et al.

Green Synthesis and Catalysis, Journal Year: 2021, Volume and Issue: 3(2), P. 194 - 197

Published: Dec. 26, 2021

Visible light promoted C–O bond formation reaction through O–H insertion of acylsilanes with oximes has been developed. The occurred under mild conditions (sole blue LED irradiation in the absence any catalysts or additives) a short time and afforded corresponding oxime ethers moderate to good yields.

Language: Английский

Citations

20

A Computational Study on the Photochemical O–H Functionalization of Alcohols with Diazoacetates DOI
Chao Pei, René M. Koenigs

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(10), P. 6832 - 6837

Published: May 2, 2022

In this computational study, we provide a detailed analysis of the underlying reaction mechanism and show that singlet carbene is initially formed. Depending on pKA alcohol, can engage in direct protonation or enol formation to yield O-H functionalization product. On contrary, propargylic alcohols take up dual role form complex with intermediate leads facile cyclopropenation reactions.

Language: Английский

Citations

13