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One-Pot Conversion of Aldehydes and Aryl Halides to Disubstituted Alkynes via Tandem Seyferth-Gilbert Homologation/Copper-Free Sonogashira Coupling. / Sapegin, Alexander; Krasavin, Mikhail.

In: Journal of Organic Chemistry, Vol. 84, No. 13, 05.07.2019, p. 8788-8795.

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

Harvard

Sapegin, A & Krasavin, M 2019, 'One-Pot Conversion of Aldehydes and Aryl Halides to Disubstituted Alkynes via Tandem Seyferth-Gilbert Homologation/Copper-Free Sonogashira Coupling', Journal of Organic Chemistry, vol. 84, no. 13, pp. 8788-8795. https://doi.org/10.1021/acs.joc.9b01367

APA

Sapegin, A., & Krasavin, M. (2019). One-Pot Conversion of Aldehydes and Aryl Halides to Disubstituted Alkynes via Tandem Seyferth-Gilbert Homologation/Copper-Free Sonogashira Coupling. Journal of Organic Chemistry, 84(13), 8788-8795. https://doi.org/10.1021/acs.joc.9b01367

Vancouver

Sapegin A, Krasavin M. One-Pot Conversion of Aldehydes and Aryl Halides to Disubstituted Alkynes via Tandem Seyferth-Gilbert Homologation/Copper-Free Sonogashira Coupling. Journal of Organic Chemistry. 2019 Jul 5;84(13):8788-8795. https://doi.org/10.1021/acs.joc.9b01367

Author

Sapegin, Alexander ; Krasavin, Mikhail. / One-Pot Conversion of Aldehydes and Aryl Halides to Disubstituted Alkynes via Tandem Seyferth-Gilbert Homologation/Copper-Free Sonogashira Coupling. In: Journal of Organic Chemistry. 2019 ; Vol. 84, No. 13. pp. 8788-8795.

BibTeX

@article{807085d71a5b4bab9c0bc4ca0582c036,
title = "One-Pot Conversion of Aldehydes and Aryl Halides to Disubstituted Alkynes via Tandem Seyferth-Gilbert Homologation/Copper-Free Sonogashira Coupling",
abstract = "A practically convenient protocol has been developed to convert a mixture of an aldehyde, aryl halide, and the Bestmann-Ohira reagent into disubstituted acetylene via a successive addition of base (Cs2CO3) and a Pd(II) catalyst, allowing sufficient time after addition of each of these reagents for the tandem processes (Seyferth-Gilbert homologation and Sonogashira coupling) to occur. Notably, for the latter reaction, no copper catalyst was required.",
keywords = "DOUBLE ELIMINATION, DIARYLACETYLENES, DIARYLALKYNES, ACETYLENES, ARYLATION, IODIDES, ACID",
author = "Alexander Sapegin and Mikhail Krasavin",
year = "2019",
month = jul,
day = "5",
doi = "10.1021/acs.joc.9b01367",
language = "English",
volume = "84",
pages = "8788--8795",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "13",

}

RIS

TY - JOUR

T1 - One-Pot Conversion of Aldehydes and Aryl Halides to Disubstituted Alkynes via Tandem Seyferth-Gilbert Homologation/Copper-Free Sonogashira Coupling

AU - Sapegin, Alexander

AU - Krasavin, Mikhail

PY - 2019/7/5

Y1 - 2019/7/5

N2 - A practically convenient protocol has been developed to convert a mixture of an aldehyde, aryl halide, and the Bestmann-Ohira reagent into disubstituted acetylene via a successive addition of base (Cs2CO3) and a Pd(II) catalyst, allowing sufficient time after addition of each of these reagents for the tandem processes (Seyferth-Gilbert homologation and Sonogashira coupling) to occur. Notably, for the latter reaction, no copper catalyst was required.

AB - A practically convenient protocol has been developed to convert a mixture of an aldehyde, aryl halide, and the Bestmann-Ohira reagent into disubstituted acetylene via a successive addition of base (Cs2CO3) and a Pd(II) catalyst, allowing sufficient time after addition of each of these reagents for the tandem processes (Seyferth-Gilbert homologation and Sonogashira coupling) to occur. Notably, for the latter reaction, no copper catalyst was required.

KW - DOUBLE ELIMINATION

KW - DIARYLACETYLENES

KW - DIARYLALKYNES

KW - ACETYLENES

KW - ARYLATION

KW - IODIDES

KW - ACID

UR - http://www.scopus.com/inward/record.url?scp=85067992545&partnerID=8YFLogxK

UR - http://www.mendeley.com/research/onepot-conversion-aldehydes-aryl-halides-disubstituted-alkynes-via-tandem-seyferthgilbert-homologati

U2 - 10.1021/acs.joc.9b01367

DO - 10.1021/acs.joc.9b01367

M3 - Article

AN - SCOPUS:85067992545

VL - 84

SP - 8788

EP - 8795

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 13

ER -

ID: 43470771