Triflic Acid Promoted Transformations of Linear-Conjugated Enynones and their Reactions with Arenes. Synthesis of Dihydropyranones, Conjugated Dienones, and Indanes

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Triflic Acid Promoted Transformations of Linear-Conjugated Enynones and their Reactions with Arenes. Synthesis of Dihydropyranones, Conjugated Dienones, and Indanes. / Zalivatskaya, Anna S.; Golovanov, Alexander A.; Boyarskaya, Irina A.; Kruykova, Mariya A.; Khoroshilova, Olesya V.; Vasilyev, Aleksander V.

In: European Journal of Organic Chemistry, Vol. 2021, No. 18, 14.05.2021, p. 2634-2649.

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

BibTeX

@article{d388d0c63ed94b3cba7cd23879563dc5,

title = "Triflic Acid Promoted Transformations of Linear-Conjugated Enynones and their Reactions with Arenes. Synthesis of Dihydropyranones, Conjugated Dienones, and Indanes",

abstract = "Linear-conjugated enynones,1,5-diarylpent-4-en-2-yn-1-ones [Ar2−CH=CH−C≡C−C(=O)Ar1], have been cyclized into 2,6-diaryl-2,3-dihydropyran-4-ones in triflic acid TfOH (CF3SO3H). Reactions of these enynones with arenes Ar3H in TfOH have afforded, at first stage, products of hydroarylation of the acetylene bond, 1,3,5-triarylpent-2,4-dien-1-ones [Ar2−CH=CH−C(Ar3)=CH−C(=O)Ar1], which have been further cyclized into alkylidene indanes. Plausible reaction mechanisms have been proposed. According to quantum chemical calculations by DFT method, initial key reactive intermediates are vinyl type dications [Ar2−CH=CH−C+=CH−C(=O+H)Ar1], generated under the protonation of carbonyl oxygen and acetylene bond of starting enynones in TfOH.",

keywords = "Conjugated dienones, Conjugated enynones, Dihydropyranones, Indanes, Triflic acid, INDANONES",

author = "Zalivatskaya, {Anna S.} and Golovanov, {Alexander A.} and Boyarskaya, {Irina A.} and Kruykova, {Mariya A.} and Khoroshilova, {Olesya V.} and Vasilyev, {Aleksander V.}",

note = "Publisher Copyright: {\textcopyright} 2021 Wiley-VCH GmbH",

year = "2021",

month = may,

day = "14",

doi = "10.1002/ejoc.202100280",

language = "English",

volume = "2021",

pages = "2634--2649",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-Blackwell",

number = "18",

}

RIS

TY - JOUR

T1 - Triflic Acid Promoted Transformations of Linear-Conjugated Enynones and their Reactions with Arenes. Synthesis of Dihydropyranones, Conjugated Dienones, and Indanes

AU - Zalivatskaya, Anna S.

AU - Golovanov, Alexander A.

AU - Boyarskaya, Irina A.

AU - Kruykova, Mariya A.

AU - Khoroshilova, Olesya V.

AU - Vasilyev, Aleksander V.

PY - 2021/5/14

Y1 - 2021/5/14

N2 - Linear-conjugated enynones,1,5-diarylpent-4-en-2-yn-1-ones [Ar2−CH=CH−C≡C−C(=O)Ar1], have been cyclized into 2,6-diaryl-2,3-dihydropyran-4-ones in triflic acid TfOH (CF3SO3H). Reactions of these enynones with arenes Ar3H in TfOH have afforded, at first stage, products of hydroarylation of the acetylene bond, 1,3,5-triarylpent-2,4-dien-1-ones [Ar2−CH=CH−C(Ar3)=CH−C(=O)Ar1], which have been further cyclized into alkylidene indanes. Plausible reaction mechanisms have been proposed. According to quantum chemical calculations by DFT method, initial key reactive intermediates are vinyl type dications [Ar2−CH=CH−C+=CH−C(=O+H)Ar1], generated under the protonation of carbonyl oxygen and acetylene bond of starting enynones in TfOH.

AB - Linear-conjugated enynones,1,5-diarylpent-4-en-2-yn-1-ones [Ar2−CH=CH−C≡C−C(=O)Ar1], have been cyclized into 2,6-diaryl-2,3-dihydropyran-4-ones in triflic acid TfOH (CF3SO3H). Reactions of these enynones with arenes Ar3H in TfOH have afforded, at first stage, products of hydroarylation of the acetylene bond, 1,3,5-triarylpent-2,4-dien-1-ones [Ar2−CH=CH−C(Ar3)=CH−C(=O)Ar1], which have been further cyclized into alkylidene indanes. Plausible reaction mechanisms have been proposed. According to quantum chemical calculations by DFT method, initial key reactive intermediates are vinyl type dications [Ar2−CH=CH−C+=CH−C(=O+H)Ar1], generated under the protonation of carbonyl oxygen and acetylene bond of starting enynones in TfOH.

KW - Conjugated dienones

KW - Conjugated enynones

KW - Dihydropyranones

KW - Indanes

KW - Triflic acid

KW - INDANONES

UR - http://www.scopus.com/inward/record.url?scp=85108285905&partnerID=8YFLogxK

U2 - 10.1002/ejoc.202100280

DO - 10.1002/ejoc.202100280

M3 - Article

AN - SCOPUS:85108285905

VL - 2021

SP - 2634

EP - 2649

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 18

ER -

ID: 85844276