Pd-Catalyzed Regioselective (Markovnikov) Addition of Aryl Boronic Acids to Terminal Alkynes of 1,3-Dicarbonyl Compounds and Cyclization/Debenzoylation of Olefinic Dicarbonyl: Access to Arylated Pyran and (E)-4-Methylene-1,6-diphenylhex-5-en-1-one

Jivan Shinde; Veerababurao Kavala; Ching Fa Yao

doi:10.1021/acs.orglett.3c02192

Pd-Catalyzed Regioselective (Markovnikov) Addition of Aryl Boronic Acids to Terminal Alkynes of 1,3-Dicarbonyl Compounds and Cyclization/Debenzoylation of Olefinic Dicarbonyl: Access to Arylated Pyran and (E)-4-Methylene-1,6-diphenylhex-5-en-1-one

Jivan Shinde, Veerababurao Kavala, Ching Fa Yao^*

^*Corresponding author for this work

Department of Chemistry

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

2 Citations (Scopus)

Abstract

This Letter outlines palladium-catalyzed regioselective (Markovnikov’s) addition of aryl boronic acids to propargyl 1,3-dicarbonyl alkyne to accomplish olefinic/diene 1,3-dicarbonyl compounds without the need for water workup. This methodology showcases remarkable performance with wide-ranging substrate diversity, achieving high yields while employing merely 3 mol % [Pd] alongside a mild KOAc base. Moreover, the utility of dicarbonyl olefins is exemplified through their application in intramolecular cyclization and debenzoylation reactions to access valuable trisubstituted pyran building blocks and (E)-4-methylene-1,6-diphenylhex-5-en-1-one synthesis.

Original language	English
Pages (from-to)	6943-6948
Number of pages	6
Journal	Organic Letters
Volume	25
Issue number	38
DOIs	https://doi.org/10.1021/acs.orglett.3c02192
Publication status	Published - 2023 Sept 29

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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CCDC 2249378: Experimental Crystal Structure Determination
Shinde, J. (Contributor), Kavala, V. (Contributor) & Yao, C. (Contributor), Cambridge Crystallographic Data Centre, 2023
DOI: 10.5517/ccdc.csd.cc2fhnl6, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc2fhnl6&sid=DataCite
Dataset
CCDC 2249380: Experimental Crystal Structure Determination
Shinde, J. (Contributor), Kavala, V. (Contributor) & Yao, C. (Contributor), Cambridge Crystallographic Data Centre, 2023
DOI: 10.5517/ccdc.csd.cc2fhnn8, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc2fhnn8&sid=DataCite
Dataset
CCDC 2249382: Experimental Crystal Structure Determination
Shinde, J. (Contributor), Kavala, V. (Contributor) & Yao, C. (Contributor), Cambridge Crystallographic Data Centre, 2023
DOI: 10.5517/ccdc.csd.cc2fhnqb, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc2fhnqb&sid=DataCite
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Shinde, J., Kavala, V., & Yao, C. F. (2023). Pd-Catalyzed Regioselective (Markovnikov) Addition of Aryl Boronic Acids to Terminal Alkynes of 1,3-Dicarbonyl Compounds and Cyclization/Debenzoylation of Olefinic Dicarbonyl: Access to Arylated Pyran and (E)-4-Methylene-1,6-diphenylhex-5-en-1-one. Organic Letters, 25(38), 6943-6948. https://doi.org/10.1021/acs.orglett.3c02192

Pd-Catalyzed Regioselective (Markovnikov) Addition of Aryl Boronic Acids to Terminal Alkynes of 1,3-Dicarbonyl Compounds and Cyclization/Debenzoylation of Olefinic Dicarbonyl: Access to Arylated Pyran and (E)-4-Methylene-1,6-diphenylhex-5-en-1-one. / Shinde, Jivan; Kavala, Veerababurao; Yao, Ching Fa.
In: Organic Letters, Vol. 25, No. 38, 29.09.2023, p. 6943-6948.

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

Shinde, J, Kavala, V & Yao, CF 2023, 'Pd-Catalyzed Regioselective (Markovnikov) Addition of Aryl Boronic Acids to Terminal Alkynes of 1,3-Dicarbonyl Compounds and Cyclization/Debenzoylation of Olefinic Dicarbonyl: Access to Arylated Pyran and (E)-4-Methylene-1,6-diphenylhex-5-en-1-one', Organic Letters, vol. 25, no. 38, pp. 6943-6948. https://doi.org/10.1021/acs.orglett.3c02192

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title = "Pd-Catalyzed Regioselective (Markovnikov) Addition of Aryl Boronic Acids to Terminal Alkynes of 1,3-Dicarbonyl Compounds and Cyclization/Debenzoylation of Olefinic Dicarbonyl: Access to Arylated Pyran and (E)-4-Methylene-1,6-diphenylhex-5-en-1-one",

abstract = "This Letter outlines palladium-catalyzed regioselective (Markovnikov{\textquoteright}s) addition of aryl boronic acids to propargyl 1,3-dicarbonyl alkyne to accomplish olefinic/diene 1,3-dicarbonyl compounds without the need for water workup. This methodology showcases remarkable performance with wide-ranging substrate diversity, achieving high yields while employing merely 3 mol % [Pd] alongside a mild KOAc base. Moreover, the utility of dicarbonyl olefins is exemplified through their application in intramolecular cyclization and debenzoylation reactions to access valuable trisubstituted pyran building blocks and (E)-4-methylene-1,6-diphenylhex-5-en-1-one synthesis.",

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AB - This Letter outlines palladium-catalyzed regioselective (Markovnikov’s) addition of aryl boronic acids to propargyl 1,3-dicarbonyl alkyne to accomplish olefinic/diene 1,3-dicarbonyl compounds without the need for water workup. This methodology showcases remarkable performance with wide-ranging substrate diversity, achieving high yields while employing merely 3 mol % [Pd] alongside a mild KOAc base. Moreover, the utility of dicarbonyl olefins is exemplified through their application in intramolecular cyclization and debenzoylation reactions to access valuable trisubstituted pyran building blocks and (E)-4-methylene-1,6-diphenylhex-5-en-1-one synthesis.

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Pd-Catalyzed Regioselective (Markovnikov) Addition of Aryl Boronic Acids to Terminal Alkynes of 1,3-Dicarbonyl Compounds and Cyclization/Debenzoylation of Olefinic Dicarbonyl: Access to Arylated Pyran and (E)-4-Methylene-1,6-diphenylhex-5-en-1-one

Abstract

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Datasets

CCDC 2249378: Experimental Crystal Structure Determination

CCDC 2249380: Experimental Crystal Structure Determination

CCDC 2249382: Experimental Crystal Structure Determination

Cite this