Transition-Metal-Free Thioboration of Terminal Alkynes DOI Creative Commons
Taro Matsuyama, H. Ishida, Chao Wang

et al.

JACS Au, Journal Year: 2024, Volume and Issue: 4(12), P. 4927 - 4933

Published: Nov. 15, 2024

We present a new type of elementoboration reaction, the thioboration terminal alkynes. This method enables highly controllable regio-/stereo-/chemoselective cis- and trans-thioboration on demand, affording synthetically versatile densely functionalized vinyl boron/vinyl sulfide derivatives in straightforward manner without need for transition-metal catalyst.

Language: Английский

Synthesis of strained, air-stable boracycles via boron–carbon-centred diradicals DOI

Xinmou Wang,

Peiqi Zhang, Zhiyi Yang

et al.

Nature Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 23, 2025

Language: Английский

Citations

1
Modular Synthesis of Complex Benzoxaboraheterocycles through Chelation-Assisted Rh-Catalyzed [2 + 2 + 2] Cycloaddition DOI Creative Commons
John M. Halford‐McGuff, Marek Varga, David B. Cordes

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(3), P. 1846 - 1854

Published: Jan. 24, 2024

Benzoxaboraheterocycles (BOBs) are moieties of increasing interest in the pharmaceutical industry; however, synthesis these compounds is often difficult or impractical due to sensitivity boron moiety, requirement for metalation–borylation protocols, and lengthy syntheses. We report a straightforward, modular approach that enables access complex examples BOB framework through Rh-catalyzed [2 + 2 2] cycloaddition using MIDA-protected alkyne boronic acids. The key development this methodology was overcoming steric barrier catalysis by leveraging chelation assistance. show utility method broad range scaffolds, mechanistic information on effect, intramolecular alcohol-assisted BMIDA hydrolysis, linear/cyclic limits as well comparative binding affinities product frameworks ribose-derived biomolecules.

Language: Английский

Citations

5
BX3-mediated borylation for the synthesis of organoboron compounds DOI
Chunhua Yang

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(23), P. 6010 - 6020

Published: Jan. 1, 2023

This review summarizes the recent progress in borylation driven by BX 3 fields of organic synthesis and drug synthesis.

Language: Английский

Citations

10
Modulation of π-Conjugation of Polymer Main Chain Containing π-Extended Benzoxaborin by Molecular Addition DOI

Shuhei Morimoto,

Kazuya Tanimura, Masayuki Gon

et al.

Macromolecules, Journal Year: 2024, Volume and Issue: 57(14), P. 6531 - 6539

Published: July 12, 2024

We synthesize novel cyclic boronic acids incorporated into the main-chain π-conjugated system. The optical measurements under basic conditions reveal that oligomer binds one-to-one to sugar containing cis-1,2-diol structure at acid moiety. In particular, binding is accompanied by a bathochromic shift in absorption and emission spectra. polymer maintained similar characteristics but showed longer wavelength region (λPL = 493–525 nm) where color change was clearly detectable before after coordination of diols. Theoretical calculations with density functional theory diol bonding moiety elevates energy levels frontier molecular orbitals, especially highest occupied orbital. This study demonstrates introduction polymers effective for detecting diols mild as well manipulating electronic structures main chains.

Language: Английский

Citations

1
Convergent Synthesis of Bicyclic Boronates via a Cascade Regioselective Suzuki-Miyaura/Cyclisation Protocol DOI Creative Commons

Alessandro Marotta,

Hannah M. Kortman,

Chiara Interdonato

et al.

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

Published: Jan. 1, 2024

A regioselective cross-coupling/cyclisation reaction of vicinal boronic esters with 2-halophenols to forge 3-substituted bicyclic boronates is disclosed enabling access drug derivatives and a pendent biomolecular probe.

Language: Английский

Citations

1
N-Directed Two-Fold Bromoboration of Diynes Enables Access to Brominated BN-Embedded PAHs DOI
Xiaoran Feng, Zhaobo Liu, Qin Ni

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 20, 2024

-directed 2-fold bromoboration reactions of diynes with BBr

Language: Английский

Citations

1
Transition-Metal-Free Thioboration of Terminal Alkynes DOI Creative Commons
Taro Matsuyama, H. Ishida, Chao Wang

et al.

JACS Au, Journal Year: 2024, Volume and Issue: 4(12), P. 4927 - 4933

Published: Nov. 15, 2024

We present a new type of elementoboration reaction, the thioboration terminal alkynes. This method enables highly controllable regio-/stereo-/chemoselective cis- and trans-thioboration on demand, affording synthetically versatile densely functionalized vinyl boron/vinyl sulfide derivatives in straightforward manner without need for transition-metal catalyst.

Language: Английский

Citations

0