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Gold-Catalyzed Oxidation of Internal Alkynes into Benzils and its Application for One-Pot Synthesis of Five-, Six-, and Seven-Membered Azaheterocycles. / Dubovtsev, Alexey Yu; Dar'in, Dmitry V.; Krasavin, Mikhail; Kukushkin, Vadim Yu.

In: European Journal of Organic Chemistry, Vol. 2019, No. 8, 28.02.2019, p. 1856-1864.

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

Harvard

Dubovtsev, AY, Dar'in, DV, Krasavin, M & Kukushkin, VY 2019, 'Gold-Catalyzed Oxidation of Internal Alkynes into Benzils and its Application for One-Pot Synthesis of Five-, Six-, and Seven-Membered Azaheterocycles', European Journal of Organic Chemistry, vol. 2019, no. 8, pp. 1856-1864. https://doi.org/10.1002/ejoc.201900108

APA

Dubovtsev, A. Y., Dar'in, D. V., Krasavin, M., & Kukushkin, V. Y. (2019). Gold-Catalyzed Oxidation of Internal Alkynes into Benzils and its Application for One-Pot Synthesis of Five-, Six-, and Seven-Membered Azaheterocycles. European Journal of Organic Chemistry, 2019(8), 1856-1864. https://doi.org/10.1002/ejoc.201900108

Vancouver

Dubovtsev AY, Dar'in DV, Krasavin M, Kukushkin VY. Gold-Catalyzed Oxidation of Internal Alkynes into Benzils and its Application for One-Pot Synthesis of Five-, Six-, and Seven-Membered Azaheterocycles. European Journal of Organic Chemistry. 2019 Feb 28;2019(8):1856-1864. https://doi.org/10.1002/ejoc.201900108

Author

Dubovtsev, Alexey Yu ; Dar'in, Dmitry V. ; Krasavin, Mikhail ; Kukushkin, Vadim Yu. / Gold-Catalyzed Oxidation of Internal Alkynes into Benzils and its Application for One-Pot Synthesis of Five-, Six-, and Seven-Membered Azaheterocycles. In: European Journal of Organic Chemistry. 2019 ; Vol. 2019, No. 8. pp. 1856-1864.

BibTeX

@article{748796391ee1448d90dd6eaa80f7cf20,
title = "Gold-Catalyzed Oxidation of Internal Alkynes into Benzils and its Application for One-Pot Synthesis of Five-, Six-, and Seven-Membered Azaheterocycles",
abstract = " Internal alkynes have been shown to undergo oxidation to substituted benzils (1,2-diarylethane-1,2-diones) by α-picoline N-oxide in the presence of Ph 3 PAuNТf 2 (5 mol-%). In addition to the unsubstituted benzil, the method allows preparing, under markedly mild conditions (50 °C in chlorobenzene), various non-symmetrical products, including heteroaromatic versions thereof which are much more difficult to obtain otherwise. This gold(I)-catalyzed transformation was integrated into one-pot reaction sequence delivering a range of 5- to 7-membered ring systems (imidazoles, quinoxalines, 1,2,4-triazines, pyrazines, and 1,4-diazepines), thus linking these important heterocyclic motifs to the internal alkyne reagent space. ",
keywords = "Gold, Heterocycles, Homogeneous catalysis, Oxidation, Synthetic methods, COMPLEXES, EFFICIENT SYNTHESIS, TERMINAL ALKYNES, CARBOXYLESTERASES, HIGHLY EFFICIENT, QUINOXALINE, INHIBITION, RING, CYCLOISOMERIZATION, DERIVATIVES",
author = "Dubovtsev, {Alexey Yu} and Dar'in, {Dmitry V.} and Mikhail Krasavin and Kukushkin, {Vadim Yu}",
year = "2019",
month = feb,
day = "28",
doi = "10.1002/ejoc.201900108",
language = "English",
volume = "2019",
pages = "1856--1864",
journal = "European Journal of Organic Chemistry",
issn = "1434-193X",
publisher = "Wiley-Blackwell",
number = "8",

}

RIS

TY - JOUR

T1 - Gold-Catalyzed Oxidation of Internal Alkynes into Benzils and its Application for One-Pot Synthesis of Five-, Six-, and Seven-Membered Azaheterocycles

AU - Dubovtsev, Alexey Yu

AU - Dar'in, Dmitry V.

AU - Krasavin, Mikhail

AU - Kukushkin, Vadim Yu

PY - 2019/2/28

Y1 - 2019/2/28

N2 - Internal alkynes have been shown to undergo oxidation to substituted benzils (1,2-diarylethane-1,2-diones) by α-picoline N-oxide in the presence of Ph 3 PAuNТf 2 (5 mol-%). In addition to the unsubstituted benzil, the method allows preparing, under markedly mild conditions (50 °C in chlorobenzene), various non-symmetrical products, including heteroaromatic versions thereof which are much more difficult to obtain otherwise. This gold(I)-catalyzed transformation was integrated into one-pot reaction sequence delivering a range of 5- to 7-membered ring systems (imidazoles, quinoxalines, 1,2,4-triazines, pyrazines, and 1,4-diazepines), thus linking these important heterocyclic motifs to the internal alkyne reagent space.

AB - Internal alkynes have been shown to undergo oxidation to substituted benzils (1,2-diarylethane-1,2-diones) by α-picoline N-oxide in the presence of Ph 3 PAuNТf 2 (5 mol-%). In addition to the unsubstituted benzil, the method allows preparing, under markedly mild conditions (50 °C in chlorobenzene), various non-symmetrical products, including heteroaromatic versions thereof which are much more difficult to obtain otherwise. This gold(I)-catalyzed transformation was integrated into one-pot reaction sequence delivering a range of 5- to 7-membered ring systems (imidazoles, quinoxalines, 1,2,4-triazines, pyrazines, and 1,4-diazepines), thus linking these important heterocyclic motifs to the internal alkyne reagent space.

KW - Gold

KW - Heterocycles

KW - Homogeneous catalysis

KW - Oxidation

KW - Synthetic methods

KW - COMPLEXES

KW - EFFICIENT SYNTHESIS

KW - TERMINAL ALKYNES

KW - CARBOXYLESTERASES

KW - HIGHLY EFFICIENT

KW - QUINOXALINE

KW - INHIBITION

KW - RING

KW - CYCLOISOMERIZATION

KW - DERIVATIVES

UR - http://www.scopus.com/inward/record.url?scp=85061434062&partnerID=8YFLogxK

UR - http://www.mendeley.com/research/goldcatalyzed-oxidation-internal-alkynes-benzils-application-onepot-synthesis-five-six-sevenmembered

U2 - 10.1002/ejoc.201900108

DO - 10.1002/ejoc.201900108

M3 - Article

AN - SCOPUS:85061434062

VL - 2019

SP - 1856

EP - 1864

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 8

ER -

ID: 39059181