Triethylborane

Yamamoto, Yoshinori; Yoshimitsu, Takehiko; Wood, John L.; Schacherer, Laura

doi:10.1002/047084289x.rt219.pub3

Cited by 2 publications

(2 citation statements)

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“…Initial studies explored the effect of the Lewis acid trimethyl borate as a reaction additive owing to its chemically benign character compared with the pyrophoricity and radical reactivity associated with alkylboranes . The initial investigation began by evaluating the effect of trimethyl borate on the Suzuki–Miyaura cross-coupling of 2-(4-bromophenyl)-1,3,4-oxadiazole 1b .…”

Section: Resultsmentioning

confidence: 99%

Heteroaryl–Heteroaryl, Suzuki–Miyaura, Anhydrous Cross-Coupling Reactions Enabled by Trimethyl Borate

et al. 2021

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Reaction conditions have been developed for refractory heteroaryl–heteroaryl Suzuki–Miyaura cross-couplings. The reported method employs neopentyl heteroarylboronic esters as nucleophiles, heteroaryl bromides and chlorides as the electrophiles, and the soluble base potassium trimethylsilanolate (TMSOK) under anhydrous conditions. The addition of trimethyl borate enhances reaction rates by several mechanisms, including (1) solubilization of in situ-generated boronate complexes, (2) preventing catalyst poisoning by the heteroatomic units, and (3) buffering the inhibitory effect of excess TMSOK. The use of this method enables cross-coupling of diverse reaction partners including a broad range of π-rich and π-deficient heteroaryl boronic esters and heteroaryl bromides. Reactions proceed in good yields and short reaction times (3 h or less).

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Section: Resultsmentioning

confidence: 99%

Heteroaryl–Heteroaryl, Suzuki–Miyaura, Anhydrous Cross-Coupling Reactions Enabled by Trimethyl Borate

et al. 2021

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“…5,6 Alkyl radicals from alkyl halides were also generated under tin free conditions specifically in the presence of triethylborane and oxygen as the radical initiator (Scheme 1b). 7,8 Over the past decade, photoredox catalysis has also become a reliable tool for the formation of these radicals under mild conditions, usually in the presence of a photocatalyst, an amine and under light irradiation (Scheme 1c). 9 Finally, alkyl radicals generation could also be carried out under catalyst-free photochemical reactions via electron donor–acceptor (EDA) complexes.…”

Section: Introductionmentioning

confidence: 99%