Photochemical Carboborylation and Three-component Difunctionalization of α,β-unsaturated Ketones with Boronic Acids via Tosylhydrazones DOI Creative Commons
Álvaro Valdés-Maqueda, Manuel Plaza, Carlos Valdés

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

The photochemical carboborylation of α,β-unsaturated tosylhydrazones with boronic acids gives tertiary allylboronates. A one pot sequence involving an aldehyde allylation provides a powerful three-component method for diversity oriented synthesis.

Language: Английский

Light-induced arylation (alkylation) of N-sulfonylhydrazones with boronic acids DOI

Mohammad Junaid,

Sharma Happy,

Dongari Yadagiri

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(20), P. 2796 - 2799

Published: Jan. 1, 2024

We report light-induced arylation (alkylation) for the synthesis of diarylmethanes, bis(diarylmethyl)benzenes, arylalkylmethanes, and triarylmethanes from readily accessible N -sulfonylhydrazones aryl/alkylboronic acids with aid Cs 2 CO 3 .

Language: Английский

Citations

6
Electrophilic Halogenation of Allenoates and 3-Alkynoates: Synthesis of 1,4-Dicarbonyl (E)-3-Haloalkenes and Mechanistic Investigations DOI
Paru Jamwal, Yumnam Nganthoinganbi, Ming‐Kang Tsai

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 26, 2025

Allenoates traditionally provide halobutenolides upon reaction with halonium ions via electrophile-assisted halolactonization. Herein, an unusual electrophilic halogenation of di- and trisubstituted allenoates 3-alkynoates is demonstrated N-halosuccinimides under DABCO promotion. The protocol affords densely functionalized 1,4-dicarbonyl 3-haloalkenes in good yields excellent (E)-stereoselectivity (up to 83% yield, >20:1 dr). are presumed form γ-haloallenoate intermediates, which further react the desired scaffolds. role nucleophilic base transformation demystified through control experiments computational studies. deliverables identified as synthons for various synthetic group transformations valuable targets biologically active pyridazine

Language: Английский

Citations

0
Facile Access to Hindered Ethers via Photoinduced O–H Bond Insertions DOI Creative Commons
Yu Zhang, Xinyu Han,

Dong Li

et al.

ACS Central Science, Journal Year: 2025, Volume and Issue: unknown

Published: April 23, 2025

Language: Английский

Citations

0
Photoactivation of Hydrazones for the Synthesis of Diarylalkanes and Trialkylmethylboronates: The Key Role Played by Soluble Base DOI
Po-Kai Peng, Clayton P. Donald,

Zhencheng Dong

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(16), P. 3397 - 3400

Published: April 11, 2024

The synthesis of diaryl alkanes and tertiary organoboronates via Barluenga coupling at room temperature occurred photoactivated conversion aryl sulfonyl hydrazones to diazo compounds in the presence soluble bases. combination arylsulfonyl hydrazone a base is necessary provide near-UV chromophore. Using aromatic boronic acids resulted rapid deboronation because instability dibenzylic boron intermediates. Alkyl allowed isolation derivatives boronate.

Language: Английский

Citations

3
Catalyst-free photoinduced C(sp3)-C(sp3) bond formation through C-H insertions using non-activated alkanes/ethers DOI
Qiannan Li,

Dinggang Wang,

Jinxin Wang

et al.

Science China Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 14, 2024

Language: Английский

Citations

2
Deoxygenative Geminal Silylboration of Amides Using Silylboronates: Synthesis and Use of α-Boryl-α-Silylalkylamines DOI Creative Commons

Koh Watanabe,

Kazunori Nagao, Hirohisa Ohmiya

et al.

Published: May 22, 2024

α-Silylalkylamines and a-borylalkylamines are versatile synthetic intermediates attractive scaffolds found in pharmaceutical drugs agrochemicals. Despite great progress on methods for preparation of α-silylalkylamines or a- borylalkylamines, there no general strategies α- boryl-α-silylalkylamines the reactivity has not been explored. Here we report deoxygenative geminal silylboration amides using silylboronates presence alkoxide base catalyst, producing boryl-a-silylalkylamines. The silicon boron groups α-boryl-α-silylalkylamines to be utilized chemoselective transformations, such as protonation alkylation. This protocol serves various α-borylalkylamines from readily available amides.

Language: Английский

Citations

1
Synthesis of Secondary Boronates via Deaminative Cross‐Coupling of Alkyl Nitroso Carbamates and Boronic Acids DOI Creative Commons
Shashwati Paul, M. Kevin Brown

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(37)

Published: Aug. 2, 2024

Abstract A strategy for transition metal‐free cross‐coupling of alkyl nitroso‐carbamates and boronic acids is reported. The N ‐nitroso carbamates are easily prepared from the corresponding amine in two simple steps. This method allows synthesis a wide variety secondary boronates, benzylic boronates formal Csp 3 −Csp 2 products under operationally conditions. Functional group tolerance also demonstrated applied modification lysine to make non‐canonical amino acids.

Language: Английский

Citations

1
Acetone Serving as a Solvent and Interaction Partner Promotes the Direct Olefination of N-Tosylhydrazones under Visible Light DOI

Dingding Xia,

Tong Li,

Xin-Yan Ke

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(9), P. 6180 - 6192

Published: April 18, 2024

The photochemistry of noncovalent interactions to promote organic transformations is an emerging approach providing fresh opportunities in synthetic chemistry. Generally, the external substance necessary add as interaction partner, thereby sacrificing atom economy reaction. Herein, we describe a catalyst-free and interaction-mediated strategy access olefination N-tosylhydrazones using acetone solvent partner. This protocol also features broad substrate scope, excellent functional group compatibility, mild reaction conditions without transition metals. Moreover, gram-scale synthesis olefins generation pharmaceutical intermediates highlighted its practical applicability. Lastly, mechanistic studies indicate that was initiated via between N-tosylhydrazone anion, which supported by density theory calculations.

Language: Английский

Citations

0
N–H Insertion of Anilines on N-Tosylhydrazones Induced by Visible Light Irradiation DOI
Clara Faure, Salim Benmaouche, Philippe Belmont

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(16), P. 11620 - 11630

Published: July 26, 2024

Diazo compounds and their precursors represent an interesting chemical category for organic synthesis. Particularly, N-tosylhydrazones have attracted attention easy accessibility diverse reactivity, including carbene transfer reactions. We described a visible light-induced N–H insertion reaction of anilines on in situ-generated diazo compounds. Optimal conditions using DBU toluene efficiently yielded the desired products. Mechanistic studies enabled us to trap intermediate that plays key role transformation.

Language: Английский

Citations

0
Synthesis of Secondary Boronates via Deaminative Cross‐Coupling of Alkyl Nitroso Carbamates and Boronic Acids DOI Creative Commons
Shashwati Paul, M. Kevin Brown

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(37)

Published: Aug. 2, 2024

Abstract A strategy for transition metal‐free cross‐coupling of alkyl nitroso‐carbamates and boronic acids is reported. The N ‐nitroso carbamates are easily prepared from the corresponding amine in two simple steps. This method allows synthesis a wide variety secondary boronates, benzylic boronates formal Csp 3 −Csp 2 products under operationally conditions. Functional group tolerance also demonstrated applied modification lysine to make non‐canonical amino acids.

Language: Английский

Citations

0