Fully Conjugated Tetraborylethylene: Selenium Mediated C–C Double Bond Formation from Diborylcarbenoid DOI Creative Commons
Yuki Shibutani, Shuhei Kusumoto, Kyoko Nozaki

et al.

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

Published: Jan. 1, 2024

Heteroatom-substituted ethylenes have long been studied owing to their potential application electronic devices. In contrast well-studied π-donor substituted ethylene, the π-acceptor one has only limitedly reported. While boron can be a candidate of π-acceptors, there still no example fully conjugated tetraborylethylene (TBE). Herein, we synthesized first TBE 2 by selenium-mediated C-C double bond formation from diborylcarbenoid 1, synthetic equivalent diborylcarbene (DBC). An intermediate bis(diborylmethylene)-λ

Language: Английский

PolyBorylated Alkenes as Energy‐Transfer Reactive Groups: Access to Multi‐Borylated Cyclobutanes Combined with Hydrogen Atom Transfer Event DOI Creative Commons
Nicole Hanania, Nadim Eghbarieh, Ahmad Masarwa

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(25)

Published: April 11, 2024

Abstract While polyborylated alkenes are being recognized for their elevated status as highly valuable reagents in modern organic synthesis, allowing efficient access to a diverse array of transformations, including the formation C−C and C‐heteroatom bonds, potential energy‐transfer reactive groups has remained unexplored. Yet, this holds key generating elusive biradical species, which can be captured by olefins, thereby leading construction new highly‐borylated scaffolds. Herein, we report designed strategy photosensitized [2+2]‐cycloadditions poly‐borylated with various olefins enabling regioselective synthesis cyclobutane motifs, 1,1‐di‐, 1,1,2‐tri‐, 1,1,2,2‐tetra‐borylated cyclobutanes. In fact, these compounds belong family that presently lacks synthetic pathways. Interestingly, when α‐methylstyrene was used, reaction involves an interesting 1,5‐hydrogen atom transfer (HAT). Mechanistic deuterium‐labeling studies have provided insight into outcome process. addition, cyclobutanes then demonstrated useful selective oxidation processes resulting cyclobutanones γ‐lactones.

Language: Английский

Citations

11
Harnessing visible light for alkenylation reactions: A promising strategy in organic synthesis DOI

M. Manod,

Archana Vijayakumar,

TS Abhinav

et al.

Molecular Catalysis, Journal Year: 2025, Volume and Issue: 579, P. 115028 - 115028

Published: March 22, 2025

Language: Английский

Citations

0
PolyBorylated Alkenes as Energy‐Transfer Reactive Groups: Access to Multi‐Borylated Cyclobutanes Combined with Hydrogen Atom Transfer Event DOI Creative Commons
Nicole Hanania, Nadim Eghbarieh, Ahmad Masarwa

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(25)

Published: April 11, 2024

Abstract While polyborylated alkenes are being recognized for their elevated status as highly valuable reagents in modern organic synthesis, allowing efficient access to a diverse array of transformations, including the formation C−C and C‐heteroatom bonds, potential energy‐transfer reactive groups has remained unexplored. Yet, this holds key generating elusive biradical species, which can be captured by olefins, thereby leading construction new highly‐borylated scaffolds. Herein, we report designed strategy photosensitized [2+2]‐cycloadditions poly‐borylated with various olefins enabling regioselective synthesis cyclobutane motifs, 1,1‐di‐, 1,1,2‐tri‐, 1,1,2,2‐tetra‐borylated cyclobutanes. In fact, these compounds belong family that presently lacks synthetic pathways. Interestingly, when α‐methylstyrene was used, reaction involves an interesting 1,5‐hydrogen atom transfer (HAT). Mechanistic deuterium‐labeling studies have provided insight into outcome process. addition, cyclobutanes then demonstrated useful selective oxidation processes resulting cyclobutanones γ‐lactones.

Language: Английский

Citations

1
Fully Conjugated Tetraborylethylene: Selenium Mediated C–C Double Bond Formation from Diborylcarbenoid DOI Creative Commons
Yuki Shibutani, Shuhei Kusumoto, Kyoko Nozaki

et al.

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

Published: Jan. 1, 2024

Heteroatom-substituted ethylenes have long been studied owing to their potential application electronic devices. In contrast well-studied π-donor substituted ethylene, the π-acceptor one has only limitedly reported. While boron can be a candidate of π-acceptors, there still no example fully conjugated tetraborylethylene (TBE). Herein, we synthesized first TBE 2 by selenium-mediated C-C double bond formation from diborylcarbenoid 1, synthetic equivalent diborylcarbene (DBC). An intermediate bis(diborylmethylene)-λ

Language: Английский

Citations

0