Blue Light-Promoted Cross-Coupling of α-Diazo Esters with Isocyanides

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Blue Light-Promoted Cross-Coupling of α-Diazo Esters with Isocyanides : Synthesis of Ester-Functionalized Ketenimines. / Sakharov, Pavel A.; Novikov, Mikhail S.; Nguyen, Tuan K.; Kinzhalov, Mikhail A.; Khlebnikov, Alexander F.; Rostovskii, Nikolai V.

In: ACS Omega, Vol. 7, No. 10, 15.03.2022, p. 9071-9079.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{311b1c195ed14575b29ec9dffe9ede44,

title = "Blue Light-Promoted Cross-Coupling of α-Diazo Esters with Isocyanides: Synthesis of Ester-Functionalized Ketenimines",

abstract = "A metal-free scalable synthesis of functionalized ketenimines from alkyl α-(aryl/heteroaryl)-α-diazoacetates and alkyl isocyanides induced by blue light irradiation has been developed. The reaction proceeds at room temperature without any photocatalyst and provides ketenimines in moderate to good yields. Density functional theory (DFT) calculations and the experimental study showed that aryl(alkoxycarbonyl)carbenes in both singlet and triplet states can react with isocyanides but only the reaction of the former leads to the smooth formation of ketenimines. The obtained ketenimines were used for the synthesis of functionalized amidines under mild metal-free conditions. ",

author = "Sakharov, {Pavel A.} and Novikov, {Mikhail S.} and Nguyen, {Tuan K.} and Kinzhalov, {Mikhail A.} and Khlebnikov, {Alexander F.} and Rostovskii, {Nikolai V.}",

note = "Publisher Copyright: {\textcopyright} 2022 The Authors. Published by American Chemical Society.",

year = "2022",

month = mar,

day = "15",

doi = "10.1021/acsomega.2c00367",

language = "English",

volume = "7",

pages = "9071--9079",

journal = "ACS Omega",

issn = "2470-1343",

publisher = "American Chemical Society",

number = "10",

}

RIS

TY - JOUR

T1 - Blue Light-Promoted Cross-Coupling of α-Diazo Esters with Isocyanides

T2 - Synthesis of Ester-Functionalized Ketenimines

AU - Sakharov, Pavel A.

AU - Novikov, Mikhail S.

AU - Nguyen, Tuan K.

AU - Kinzhalov, Mikhail A.

AU - Khlebnikov, Alexander F.

AU - Rostovskii, Nikolai V.

PY - 2022/3/15

Y1 - 2022/3/15

N2 - A metal-free scalable synthesis of functionalized ketenimines from alkyl α-(aryl/heteroaryl)-α-diazoacetates and alkyl isocyanides induced by blue light irradiation has been developed. The reaction proceeds at room temperature without any photocatalyst and provides ketenimines in moderate to good yields. Density functional theory (DFT) calculations and the experimental study showed that aryl(alkoxycarbonyl)carbenes in both singlet and triplet states can react with isocyanides but only the reaction of the former leads to the smooth formation of ketenimines. The obtained ketenimines were used for the synthesis of functionalized amidines under mild metal-free conditions.

AB - A metal-free scalable synthesis of functionalized ketenimines from alkyl α-(aryl/heteroaryl)-α-diazoacetates and alkyl isocyanides induced by blue light irradiation has been developed. The reaction proceeds at room temperature without any photocatalyst and provides ketenimines in moderate to good yields. Density functional theory (DFT) calculations and the experimental study showed that aryl(alkoxycarbonyl)carbenes in both singlet and triplet states can react with isocyanides but only the reaction of the former leads to the smooth formation of ketenimines. The obtained ketenimines were used for the synthesis of functionalized amidines under mild metal-free conditions.

UR - http://www.scopus.com/inward/record.url?scp=85126803168&partnerID=8YFLogxK

U2 - 10.1021/acsomega.2c00367

DO - 10.1021/acsomega.2c00367

M3 - Article

AN - SCOPUS:85126803168

VL - 7

SP - 9071

EP - 9079

JO - ACS Omega

JF - ACS Omega

SN - 2470-1343

IS - 10

ER -

ID: 95277676

Blue Light-Promoted Cross-Coupling of α-Diazo Esters with Isocyanides: Synthesis of Ester-Functionalized Ketenimines

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