The Aryne Phosphate Reaction** DOI
Thomas Haas, Stefan Wiesler, Tobias Dürr‐Mayer

и другие.

Angewandte Chemie, Год журнала: 2021, Номер 134(1)

Опубликована: Ноя. 2, 2021

Abstract Condensed phosphates are a critically important class of molecules in biochemistry. Non‐natural analogues for various applications, such as single‐molecule real‐time DNA sequencing. Often, contain more than three phosphate units their oligophosphate chain. Consequently, investigations into reactivity enabling new ways functionalization and oligophosphorylation essential. Here, we scrutinize the potential to act arynophiles, paving way follow‐up reactions. The aryne reaction is powerful tool to—depending on perspective—(oligo)phosphorylate arenes or arylate (oligo‐cyclo)phosphates. Based Kobayashi‐type o‐silylaryltriflates, enables rapid entry broad spectrum arylated products, like monophosphates, diphosphates, phosphodiesters polyphosphates. synthetic these transformations demonstrated by efficient syntheses nucleotide an unprecedented one‐flask octaphosphorylation.

Язык: Английский

Aryne‐Enabled C−N Arylation of Anilines DOI Creative Commons
Thomas Sephton, Anastasios Charitou, Cristina Trujillo

и другие.

Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(49)

Опубликована: Окт. 18, 2023

Abstract Anilines are potentially high‐value arylating agents, but limited by the low reactivity of strong C−N bond. We show that reactive intermediate benzyne can be used to both activate anilines, and set‐up an aryl transfer reaction in a single step. The does not require any transition metal catalysts or stoichiometric organometallics, establishes metal‐free route valuable biaryl products functionalizing aniline

Язык: Английский

Процитировано

11

The Aryne Phosphate Reaction** DOI
Thomas Haas, Stefan Wiesler, Tobias Dürr‐Mayer

и другие.

Angewandte Chemie International Edition, Год журнала: 2021, Номер 61(1)

Опубликована: Ноя. 2, 2021

Condensed phosphates are a critically important class of molecules in biochemistry. Non-natural analogues for various applications, such as single-molecule real-time DNA sequencing. Often, contain more than three phosphate units their oligophosphate chain. Consequently, investigations into reactivity enabling new ways functionalization and oligophosphorylation essential. Here, we scrutinize the potential to act arynophiles, paving way follow-up reactions. The aryne reaction is powerful tool to-depending on perspective-(oligo)phosphorylate arenes or arylate (oligo-cyclo)phosphates. Based Kobayashi-type o-silylaryltriflates, enables rapid entry broad spectrum arylated products, like monophosphates, diphosphates, phosphodiesters polyphosphates. synthetic these transformations demonstrated by efficient syntheses nucleotide an unprecedented one-flask octaphosphorylation.

Язык: Английский

Процитировано

14

Quinquevalent phosphorus acids DOI
Piotr Bałczewski, Krzysztof Owsianik

Royal Society of Chemistry eBooks, Год журнала: 2024, Номер unknown, С. 109 - 231

Опубликована: Фев. 21, 2024

This chapter shows, as in previous years, the most important achievements of 2021 year area organo-phosphorus compounds containing: three P–O bonds (Section 2: phosphoric acids and their derivatives), two one P–C 3: phosphonic derivatives) well 4: phosphinic addition to phosphoryl group P═O, present all groups compounds. Each main sections covers “synthesis reactions” including pure synthesis without applications, biological applications” miscellaneous directed towards non-biological applications. At end each subsection, corresponding are shown for hetero-analogues which phosphorus–oxygen have been replaced by phosphorus–heteroatom P–X and/or P═Y (X, Y = N, S or Se). The subsection on quinquevalent phosphorus derivatives catalysts has placed, usual, at entire chapter, after a review As devoted dominated over smaller section derivatives, literature references these remained ratio 4 : 12 1. A dynamic, five-fold increase number works, subject chiral catalysts, recorded this year.

Язык: Английский

Процитировано

1

Synthesis of Multisubstituted Aromatics via 3-Triazenylarynes DOI
Jumpei Taguchi, Takumi Okuyama,

Satomi Tomita

и другие.

Organic Letters, Год журнала: 2023, Номер 25(38), С. 7030 - 7034

Опубликована: Сен. 15, 2023

An efficient method for generating 3-triazenylarynes from ortho-iodoaryl triflate-type precursors was developed. The generated arynes reacted with various arynophiles high regioselectivity because of the triazenyl group. 3-triazenylaryne functioned as useful intermediates diverse multisubstituted aromatic compounds through transformation remaining group aryne adducts and group-directed ortho-C-H functionalization.

Язык: Английский

Процитировано

3

Practical Synthesis of Tenofovir Alafenamide Fumarate Inspired by New Retrosynthetic Disconnection Featuring a Novel Carbon–Phosphorus Bond Construction Methodology DOI
Xiuping Liu, Chen Chen, Muzi Li

и другие.

Organic Process Research & Development, Год журнала: 2023, Номер 27(6), С. 1079 - 1093

Опубликована: Май 19, 2023

Tenofovir alafenamide fumarate (TAF) is rising as a mainstay antiretroviral agent for the treatment of HIV and chronic HBV infections. A de novo practical synthesis TAF circumventing tenofovir (PMPA) has been accomplished on 7 g scale. This reimagined TAF, inspired by hitherto uncharted retrosynthetic disconnection, centers P-alkylation silylated diphenyl phosphonate 11 (as acceptor) with methylthiomethyl (MTM) ether derivative 12 donor) in presence NIS/TfOH combination promoter to construct strategic carbon–phosphorus bond. PMPA-free not only removes intrinsic drawbacks encountered PMPA-dependent commercial process but also beneficial diversification synthetic portfolio TAF. Furthermore, this type reaction defined stereochemistry could be deployed late-stage modification druglike molecules natural products access valuable derivatives.

Язык: Английский

Процитировано

2

Aryne‐Enabled C−N Arylation of Anilines DOI Creative Commons
Thomas Sephton, Anastasios Charitou, Cristina Trujillo

и другие.

Angewandte Chemie, Год журнала: 2023, Номер 135(49)

Опубликована: Окт. 18, 2023

Abstract Anilines are potentially high‐value arylating agents, but limited by the low reactivity of strong C−N bond. We show that reactive intermediate benzyne can be used to both activate anilines, and set‐up an aryl transfer reaction in a single step. The does not require any transition metal catalysts or stoichiometric organometallics, establishes metal‐free route valuable biaryl products functionalizing aniline

Язык: Английский

Процитировано

2

Development of 3-triazenylaryne and its application to iterative aryne reactions via o-triazenylarylboronic acids DOI
Motoki Ito,

Yuta Takishima,

Rinto Ishikawa

и другие.

Chemical Communications, Год журнала: 2023, Номер 59(96), С. 14249 - 14252

Опубликована: Янв. 1, 2023

A novel aryne species 3-triazenylaryne has been developed as a divergent platform for the generation of 3-alkynylaryne through o -triazenylarylboronic acids.

Язык: Английский

Процитировано

2

3-Azidoarynes: Generation and Regioselective Reactions DOI Open Access
Jumpei Taguchi,

Kota Kimura,

Kazunobu Igawa

и другие.

Chemistry Letters, Год журнала: 2021, Номер 51(2), С. 94 - 98

Опубликована: Ноя. 19, 2021

Abstract The generation of 3-azidoarynes from o-iodoaryl triflate-type precursors was achieved using a silylmethyl Grignard reagent as the activator. azido group served to control regioselectivity reaction with arynophiles. remaining in adduct also transformable functional group, enabling further derivatization various nitrogen-containing compounds.

Язык: Английский

Процитировано

5

Synthetic Strategies toward Ortho-3-propanoate Substituted Aryl Phosphonates by Three-Component Coupling Reactions of Arynes, Phosphites, and Acrylates DOI
Donghwa Shin, Soomin Kim, Duck‐Hyung Lee

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(11), С. 8035 - 8040

Опубликована: Май 28, 2024

Mild, metal-free, and operationally simple three-component coupling reactions involving arynes, phosphites, acrylates have been achieved. The reaction proceeded well with α- or β-substituted acrylates. Additionally, various functional groups were tolerated under these conditions, resulting in diverse

Язык: Английский

Процитировано

0

Regioselective transformation of 3-phosphoryl benzyne intermediates to diverse phosphorus-substituted arenes DOI
Jing Wang,

Zenghui Li,

Gaoqiang You

и другие.

New Journal of Chemistry, Год журнала: 2022, Номер 46(35), С. 17049 - 17054

Опубликована: Янв. 1, 2022

Pre-functionalized benzyne precursors 5 , 6 and 10 bearing a phosphoryl group were efficiently synthesized via phospho-Fries rearrangement reaction on gram scales, directly proceed various transformations to poly-substituted organophosphorus arenes in high regioselectivity.

Язык: Английский

Процитировано

0