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The Dichotomy of Gold-catalyzed Interplay between Cyanamides and Ynamides : Controllable Switch from [2+2+2] to [4+2] Cycloaddition. / Dubovtsev, Alexey Yu; Shcherbakov, Nikolay V.; Dar'in, Dmitry V.; Kukushkin, Vadim Yu.

In: Advanced Synthesis and Catalysis, Vol. 362, No. 13, 16.07.2020, p. 2672-2682.

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

Harvard

Dubovtsev, AY, Shcherbakov, NV, Dar'in, DV & Kukushkin, VY 2020, 'The Dichotomy of Gold-catalyzed Interplay between Cyanamides and Ynamides: Controllable Switch from [2+2+2] to [4+2] Cycloaddition', Advanced Synthesis and Catalysis, vol. 362, no. 13, pp. 2672-2682. https://doi.org/10.1002/adsc.202000434

APA

Dubovtsev, A. Y., Shcherbakov, N. V., Dar'in, D. V., & Kukushkin, V. Y. (2020). The Dichotomy of Gold-catalyzed Interplay between Cyanamides and Ynamides: Controllable Switch from [2+2+2] to [4+2] Cycloaddition. Advanced Synthesis and Catalysis, 362(13), 2672-2682. https://doi.org/10.1002/adsc.202000434

Vancouver

Dubovtsev AY, Shcherbakov NV, Dar'in DV, Kukushkin VY. The Dichotomy of Gold-catalyzed Interplay between Cyanamides and Ynamides: Controllable Switch from [2+2+2] to [4+2] Cycloaddition. Advanced Synthesis and Catalysis. 2020 Jul 16;362(13):2672-2682. https://doi.org/10.1002/adsc.202000434

Author

Dubovtsev, Alexey Yu ; Shcherbakov, Nikolay V. ; Dar'in, Dmitry V. ; Kukushkin, Vadim Yu. / The Dichotomy of Gold-catalyzed Interplay between Cyanamides and Ynamides : Controllable Switch from [2+2+2] to [4+2] Cycloaddition. In: Advanced Synthesis and Catalysis. 2020 ; Vol. 362, No. 13. pp. 2672-2682.

BibTeX

@article{acc68aae051b4c119752e4244c2a5198,
title = "The Dichotomy of Gold-catalyzed Interplay between Cyanamides and Ynamides: Controllable Switch from [2+2+2] to [4+2] Cycloaddition",
abstract = "The gold-catalyzed interplay between cyanamides and ynamides demonstrates condition-dependent mechanistic dichotomy. [2+2+2] Cycloaddition proceeds under kinetically controlled conditions to give 2,4,6-triaminopyrimidines (19 examples, up to 99%). Under thermodynamically controlled conditions, the reactivity switches from [2+2+2]- to [4+2] cycloaddition; the latter [4+2] reaction accomplishes 1,3-diaminoisoquinolines (19 examples, up to 97%). The advantages of both methods include regioselectivity, mild reaction conditions (even for the thermodynamically controlled [4+2] reaction) and the possibility of introducing a variety of dialkyl, diaryl, and heterocyclic amino substituents into the target pyrimidine and isoquinoline cores. The reactions were conducted on gram scales and the versatility of the obtained products was demonstrated by post-functionalizations. (Figure presented.).",
keywords = "Cycloaddition, Gold catalysis, Heterocycles, Homogeneous catalysis, Synthetic methods, PLATINUM, ALKYNES, ALLENAMIDES, NITRILES, CARBENES, OXIDATIVE CYCLIZATION, FACILE, EFFICIENT",
author = "Dubovtsev, {Alexey Yu} and Shcherbakov, {Nikolay V.} and Dar'in, {Dmitry V.} and Kukushkin, {Vadim Yu}",
year = "2020",
month = jul,
day = "16",
doi = "10.1002/adsc.202000434",
language = "English",
volume = "362",
pages = "2672--2682",
journal = "Advanced Synthesis and Catalysis",
issn = "1615-4150",
publisher = "Wiley-Blackwell",
number = "13",

}

RIS

TY - JOUR

T1 - The Dichotomy of Gold-catalyzed Interplay between Cyanamides and Ynamides

T2 - Controllable Switch from [2+2+2] to [4+2] Cycloaddition

AU - Dubovtsev, Alexey Yu

AU - Shcherbakov, Nikolay V.

AU - Dar'in, Dmitry V.

AU - Kukushkin, Vadim Yu

PY - 2020/7/16

Y1 - 2020/7/16

N2 - The gold-catalyzed interplay between cyanamides and ynamides demonstrates condition-dependent mechanistic dichotomy. [2+2+2] Cycloaddition proceeds under kinetically controlled conditions to give 2,4,6-triaminopyrimidines (19 examples, up to 99%). Under thermodynamically controlled conditions, the reactivity switches from [2+2+2]- to [4+2] cycloaddition; the latter [4+2] reaction accomplishes 1,3-diaminoisoquinolines (19 examples, up to 97%). The advantages of both methods include regioselectivity, mild reaction conditions (even for the thermodynamically controlled [4+2] reaction) and the possibility of introducing a variety of dialkyl, diaryl, and heterocyclic amino substituents into the target pyrimidine and isoquinoline cores. The reactions were conducted on gram scales and the versatility of the obtained products was demonstrated by post-functionalizations. (Figure presented.).

AB - The gold-catalyzed interplay between cyanamides and ynamides demonstrates condition-dependent mechanistic dichotomy. [2+2+2] Cycloaddition proceeds under kinetically controlled conditions to give 2,4,6-triaminopyrimidines (19 examples, up to 99%). Under thermodynamically controlled conditions, the reactivity switches from [2+2+2]- to [4+2] cycloaddition; the latter [4+2] reaction accomplishes 1,3-diaminoisoquinolines (19 examples, up to 97%). The advantages of both methods include regioselectivity, mild reaction conditions (even for the thermodynamically controlled [4+2] reaction) and the possibility of introducing a variety of dialkyl, diaryl, and heterocyclic amino substituents into the target pyrimidine and isoquinoline cores. The reactions were conducted on gram scales and the versatility of the obtained products was demonstrated by post-functionalizations. (Figure presented.).

KW - Cycloaddition

KW - Gold catalysis

KW - Heterocycles

KW - Homogeneous catalysis

KW - Synthetic methods

KW - PLATINUM

KW - ALKYNES

KW - ALLENAMIDES

KW - NITRILES

KW - CARBENES

KW - OXIDATIVE CYCLIZATION

KW - FACILE

KW - EFFICIENT

UR - http://www.scopus.com/inward/record.url?scp=85085123467&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/f3b48f9f-45b6-3926-a4ee-50bf689469e6/

U2 - 10.1002/adsc.202000434

DO - 10.1002/adsc.202000434

M3 - Article

AN - SCOPUS:85085123467

VL - 362

SP - 2672

EP - 2682

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

SN - 1615-4150

IS - 13

ER -

ID: 60792850