One-Pot Sequential Alcohol Activation and Nickel-Catalyzed Cross-Electrophile Coupling with Chlorosilanes DOI Creative Commons

Xiaojie Liu,

Biping Xu, Martin Oestreich

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 31, 2025

A formal deoxygenative silylation of primary alcohols is reported. The one-pot procedure consists an in situ bromination the alcohol and a subsequent nickel-catalyzed cross-electrophile coupling formed alkyl bromide various vinyl-substituted chlorosilanes. key to success compatibility nickel catalysis as well chlorosilane electrophile with byproducts preceding step, especially triphenylphosphine oxide likely acting weak ligand for excess catalyst used.

Language: Английский

Photocatalytic Oxidative Hydroacylation with Alcohols DOI

Sabhya Sandha,

Chandra Bhushan Tripathi

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A photocatalytic oxidative hydroacylation with alcohols for C–N and C–C bond formation is reported.

Language: Английский

Citations

0
Nickel-Catalyzed Cross-Electrophile Coupling of Aryl Triflates with Alkyl Halides: Mechanism-Informed Design of More General Conditions DOI
Seoyoung Kim, Matthew J. Goldfogel, Benjamin N. Ahern

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 10, 2025

Aryl triflates make up a class of aryl electrophiles that are available in single step from the corresponding phenol. Despite known reactivity nickel complexes for C-O bond activation phenol derivatives, nickel-catalyzed cross-electrophile coupling using has proven challenging. Herein, we report method to form C(sp2)-C(sp3) bonds by with alkyl bromides and chlorides phenanthroline (phen) or pyridine-2,6-bis(N-cyanocarboxamidine) (PyBCamCN)-ligated catalysts. The scope reaction is demonstrated 38 examples (61 ± 14% average yield). Mechanistic studies provide rationale conditions used roadmap further applications coupling. First, rate radical generation controlled maintaining majority halide as chloride, which unreactive, utilizing dynamic exchange process adjust concentration reactive bromide iodide. Second, challenge electron-rich appears be due off-cycle transmetalation unproductive zinc reagents. optimal PyBCamCN ligand together LiCl avoids this deleterious step.

Language: Английский

Citations

0
One-Pot Chlorination and Cross-Electrophile Coupling of Alcohols with Aryl Chlorides DOI
Benjamin N. Ahern, Daniel J. Weix

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 24, 2025

Although alkyl alcohols and aryl chlorides are the two most abundant substrate pools for cross-electrophile coupling, methods to couple them remain limited. Herein we demonstrate a simple procedure in situ deoxychlorination of followed by XEC with chlorides. A broad scope can be achieved tuning rate reaction via halide exchange. Key success is identification 1-chloro-N,N,2-trimethyl-1-propenylamine as mild, noninterfering halogenation reagent.

Language: Английский

Citations

0
One-Pot Sequential Alcohol Activation and Nickel-Catalyzed Cross-Electrophile Coupling with Chlorosilanes DOI Creative Commons

Xiaojie Liu,

Biping Xu, Martin Oestreich

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 31, 2025

A formal deoxygenative silylation of primary alcohols is reported. The one-pot procedure consists an in situ bromination the alcohol and a subsequent nickel-catalyzed cross-electrophile coupling formed alkyl bromide various vinyl-substituted chlorosilanes. key to success compatibility nickel catalysis as well chlorosilane electrophile with byproducts preceding step, especially triphenylphosphine oxide likely acting weak ligand for excess catalyst used.

Language: Английский

Citations

0