2022
DOI: 10.1021/acs.orglett.2c00877
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Photochemical Nozaki–Hiyama–Kishi Coupling Enabled by Excited Hantzsch Ester

Abstract: This work reports the first photochemical Nozaki−Hiyama−Kishi coupling enabled by bioinspired Hantzsch ester. The salient feature of this process is that commercially available and low-cost organic photoactive Hantzsch ester can serve as both an electron and a proton donor to reduce Cr/Ni to lowvalent species and hydrolyze the Cr III -alkoxy bond, thus bypassing the use of stoichiometric metallic reductants and additives such as TMSCl and Cp 2 ZrCl 2 . The mild conditions and operationally easy method showed b… Show more

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Cited by 13 publications
(9 citation statements)
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“…HEH has been widely used as an organic hydrogen reductant in hydrogenation reactions. 14–16 Herein, we use the XH/HB pair strategy to obtain thermodynamically equivalent hydrogen reductants to HEH. The Gibbs free energy of HEH releasing two hydrogen ions, Δ G PH − (HEH), is determined as 83.1 kcal mol −1 in acetonitrile by combining Δ G H − D (HEH) (64.4 kcal mol −1 ) 3 d and p K a (HE + ) (13.65).…”
Section: Resultsmentioning
confidence: 99%
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“…HEH has been widely used as an organic hydrogen reductant in hydrogenation reactions. 14–16 Herein, we use the XH/HB pair strategy to obtain thermodynamically equivalent hydrogen reductants to HEH. The Gibbs free energy of HEH releasing two hydrogen ions, Δ G PH − (HEH), is determined as 83.1 kcal mol −1 in acetonitrile by combining Δ G H − D (HEH) (64.4 kcal mol −1 ) 3 d and p K a (HE + ) (13.65).…”
Section: Resultsmentioning
confidence: 99%
“…As seen from Scheme 8, the Δ G PH − (XH/HB) scale of 14 472 (216 XHs × 67 HBs) XH/HB pairs spans a very wide range of 107.2 kcal mol −1 , and all kinds of XH/HB pairs with different reduction abilities from 42.1 to 149.3 kcal mol −1 could be designed to hydrogenate various unsaturated substrates. Since HCO 2 H (70.1 kcal mol −1 ), 18 H 2 (76.0 kcal mol −1 ), 12 HEH (83.1 kcal mol −1 ) 3 d and i PrOH (84.3 kcal mol −1 ) 19 are excellent hydrogen reductants to be extensively applied in hydrogenation reactions, 14–16,20–22 it is convincing to deduce that many XH/HB pairs (42.1–149.3 kcal mol −1 ) are thermodynamically better hydrogen reductants than common excellent hydrogen reductants to be their better alternatives in hydrogenation reactions.…”
Section: Resultsmentioning
confidence: 99%
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