Access to Diarylmethanols by Wittig Rearrangement of ortho-, meta-, and para-Benzyloxy-N-Butylbenzamides

Aitken, R. A.; Harper, Andrew D.; Inwood, Ryan A.; Slawin, Alexandra M. Z.

doi:10.1021/acs.joc.1c03160

Cited by 7 publications

(6 citation statements)

References 64 publications

(50 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The authors have cited additional references within the Supporting Information. [59][60][61][62][63][64][65]…”

Section: Discussionmentioning

confidence: 99%

Photocatalytic metal‐free oxidation of alcohols with molecular oxygen in supercritical CO₂ medium

Merkulov,

Zharkov,

Turova

et al. 2024

ChemPhotoChem

View full text Add to dashboard Cite

Near‐UV‐light‐induced oxidative conversion of cyclic and linear alcohols into corresponding carbonyl compounds was achieved in the supercritical CO2 medium under the action of molecular oxygen in the presence of 2‐fluoroanthraquinone (1 mol%), a simple and available metal‐free photocatalyst. A thorough examination of the impact of various process parameters on the reaction outcome allowed to identify a narrow density area at ~0.3 g/cm3 in the vicinity of the medium critical point and optimal reaction conditions (~45°C, ~8.4 MPa) where up to 99% conversions and 65‐93% yields of the oxidation products could be attained. Furthermore, it has been shown that compressed atmospheric air, a far cheaper and safer oxidizer than pure oxygen, can be applied to the reaction. Based on the experimental data, a plausible mechanism of the photocatalytic process has been proposed comprising photocatalyst excitation with near‐UV light followed by the hydrogen atom transfer (HAT) as the key stages.

show abstract

“…The authors have cited additional references within the Supporting Information. [59][60][61][62][63][64][65]…”

Section: Discussionmentioning

confidence: 99%

Photocatalytic metal‐free oxidation of alcohols with molecular oxygen in supercritical CO₂ medium

Merkulov,

Zharkov,

Turova

et al. 2024

ChemPhotoChem

View full text Add to dashboard Cite

show abstract

“…62 Finally the n-butyl amide group was found to promote the rearrangement in moderate to high yield and was effective in ortho-, meta-, and para-positions giving diarylmethanol products 70. 63 This method has since been extended to the phosphonamide directing group giving 71, 64 and further studies on oxazoline-based systems have also been reported. 65 Arising from a fundamental study on FVP of a-functionalised carboxylic acid derivatives, dioxolanones derived from lactic or mandelic acid were found to be effective chiral acyl anion equivalents.…”

Section: O Phmentioning

confidence: 99%

A tribute to Professor Aitken

Karodia

2023

Arkivoc

View full text Add to dashboard Cite

Robert Alan Aitken was born on 27th March 1958 to a farming family in the Dumfries and Galloway area of Southwest Scotland. Despite his rural upbringing, he was not the first scientist in the family since his great grandfather's younger brother, Edward Hamilton Aitken ("EHA", 1851("EHA", -1909, was a noted author and naturalist in India in the days of the Raj and a founder member and first Secretary (1883-1886) of the Bombay Natural History Society. He gave his name to several biological species including five species of Indian ant and a mosquito Anopheles aitkenii. When it came time for university, Alan followed the example of the only previous family member to go to a UK university, his paternal grandmother Rona Macrae (MA, 1925), and went to the University of Edinburgh. There he completed a BSc (1979) with a final year research project on stabilised phosphonium ylides and this was followed by a PhD (1982) on flash vacuum pyrolysis of cyclic sulfones, both projects jointly supervised by Dr Ian Gosney and Professor J. I. G. (later Sir John) Cadogan. He then obtained a Fulbright Scholarship for postdoctoral studies with Professor Albert I. Meyers at Colorado State University, Fort Collins (1982-84) in the area of asymmetric synthesis using nitrogen heterocycles. In 1984 he was awarded a Royal Society Warren Research Fellowship and joined the staff at the University of St Andrews, the first new staff appointment there since 1972. He has remained there ever since and is currently Reader in Organic Chemistry. He has been a Fellow of the Royal Society of Chemistry since 1997.Alan has maintained a small but productive research group and has so far supervised the research of 10 postdoctoral researchers, 29 PhD students, 9 MSc and MPhil students and 145 undergraduate project students. These include coworkers from over 20 countries: Belgium,

show abstract

“…More recently, we discovered the N-butylcarboxamide CONHBu as a more efficient and general activating group, allowing the Wittig rearrangement of ortho-, meta-, or paraoriented benzylic ethers 5 to afford diarylmethanols 6 [6]. A limited degree of success in using a chiral secondary amide group to bring about asymmetric Wittig rearrangement was also described [7].…”

Section: Introductionmentioning

confidence: 99%

“…Organics 2024, 5, FOR PEER REVIEW 2 Scheme 1. General strategy for indirect C-C bond formation via ether formation and Wittig rearrangement and previously reported examples [4,6].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Butyllithium-Induced Cyclisation of 2-Benzyloxyphenylphosphonamidates Giving 2,3-Dihydrobenzo[d][1,3]oxaphospholes

Aitken,

Ait Moulay,

Cordes

et al. 2024

Organics

Self Cite

View full text Add to dashboard Cite

A series of fourteen O-ethyl-N-butylphenylphosphonamidates with benzyl ether substituents at the ortho position was prepared and fully characterised. Upon treatment with n-butyllithium in THF at RT, they underwent cyclisation in eight cases to give the novel 2,3-dihydrobenzo[d][1,3]oxaphospholes in moderate to low yield as a single diastereomer, for which the relative configuration was determined by X-ray diffraction in one case.

show abstract

Access to Diarylmethanols by Wittig Rearrangement of ortho-, meta-, and para-Benzyloxy-N-Butylbenzamides

Cited by 7 publications

References 64 publications

Photocatalytic metal‐free oxidation of alcohols with molecular oxygen in supercritical CO₂ medium

Photocatalytic metal‐free oxidation of alcohols with molecular oxygen in supercritical CO₂ medium

A tribute to Professor Aitken

Synthesis and Butyllithium-Induced Cyclisation of 2-Benzyloxyphenylphosphonamidates Giving 2,3-Dihydrobenzo[d][1,3]oxaphospholes

Contact Info

Product

Resources

About

Access to Diarylmethanols by Wittig Rearrangement of ortho-, meta-, and para-Benzyloxy-N-Butylbenzamides

Cited by 7 publications

References 64 publications

Photocatalytic metal‐free oxidation of alcohols with molecular oxygen in supercritical CO2 medium

Photocatalytic metal‐free oxidation of alcohols with molecular oxygen in supercritical CO2 medium

A tribute to Professor Aitken

Synthesis and Butyllithium-Induced Cyclisation of 2-Benzyloxyphenylphosphonamidates Giving 2,3-Dihydrobenzo[d][1,3]oxaphospholes

Contact Info

Product

Resources

About

Photocatalytic metal‐free oxidation of alcohols with molecular oxygen in supercritical CO₂ medium

Photocatalytic metal‐free oxidation of alcohols with molecular oxygen in supercritical CO₂ medium