Related Experiment Video
Updated: Sep 13, 2025

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
Photoinduced EDA Complex-Enabled Deboronative Arylation of Potassium Alkyltrifluoroborates
Anping Luo1, Jiaxin Yang1, Wenjie Liu1
1School of Pharmacy, Southwest Medical University, Luzhou 646000, People's Republic of China.
Abstract:
The green synthesis chemistry mediated by photoinduced electron donor-acceptor (EDA) chemistry is highly compelling and desirable in both academic and industrial applications. Herein, an EDA complex-enabled deboronative arylation was established by using readily available potassium alkyltrifluoroborates and (hetero)aryl nitriles under mild conditions, eliminating the need for photocatalysts, transition metals, bases, and oxidants. Mechanistic investigations provided insights into the formation of a novel EDA complex involving alkyltrifluoroborates and aryl nitriles. Under light irradiation, a wide range of 1°, 2°, and 3° alkyltrifluoroborates can serve as carbon-centered radical precursors, enabling the formation of new C(sp3)-C(sp2) bonds, leading to the synthesis of a wide variety of valuable alkylarene derivatives with moderate to excellent yields.
Related Concept Videos
Hydroboration-Oxidation of Alkenes
Aldol Condensation with β-Diesters: Knoevenagel Condensation
α-Alkylation of Ketones via Enolate Ions
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
E2 Reaction: Kinetics and Mechanism
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.

