Decarboxylative Conjunctive Cross-coupling of Vinyl Boronic Esters using Metallaphotoredox Catalysis

Riccardo S. Mega; Vincent K. Duong; Adam Noble; Varinder Kumar Aggarwal

doi:10.1002/anie.201916340

Decarboxylative Conjunctive Cross-coupling of Vinyl Boronic Esters using Metallaphotoredox Catalysis

Riccardo S. Mega, Vincent K. Duong, Adam Noble^*, Varinder Kumar Aggarwal^*

^*Corresponding author for this work

Research output: Contribution to journal › Article (Academic Journal) › peer-review

129 Citations (Scopus)

369 Downloads (Pure)

Abstract

The synthesis of complex alkyl boronic esters via a conjunctive cross‐coupling of vinyl boronic esters with carboxylic acids and aryl iodides is described. The reaction proceeds under mild metallaphotoredox conditions and involves an unprecedented decarboxylative radical addition/cross‐coupling cascade of vinyl boronic esters. Excellent functional group tolerance is displayed, and application of a range of carboxylic acids, namely secondary α‐amino acids, and aryl iodides provides efficient access to highly functionalized alkyl boronic esters. The decarboxylative conjunctive cross‐coupling was also applied to the synthesis of sedum alkaloids.

Original language	English
Pages (from-to)	4375-4379
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	59
Issue number	11
Early online date	3 Feb 2020
DOIs	https://doi.org/10.1002/anie.201916340
Publication status	Published - 9 Mar 2020

Research Groups and Themes

Organic & Biological

Keywords

metallaphotoredox catalysis
decarboxylative crosscoupling
conjunctive cross-coupling
alkyl boronic esters
carboxylic acids

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10.1002/anie.201916340

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This is the author accepted manuscript (AAM). The final published version (version of record) is available online via Wiley at https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201916340. Please refer to any applicable terms of use of the publisher.
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FRESCO: Efficient, Flexible Synthesis of Molecules with Tailored Shapes: from Photoswitchable Helices to anti-Cancer Compounds
Aggarwal, V. K. (Principal Investigator)
1/10/15 → 31/03/21
Project: Research

Decarboxylative Radical Additions to Vinyl Boronic Esters
Mega, R. S. (Author), Aggarwal, V. (Supervisor), 29 Sept 2020
Student thesis: Doctoral Thesis › Doctor of Philosophy (PhD)

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@article{4f67926cc1b04e1084fa9c1bf214da93,

title = "Decarboxylative Conjunctive Cross-coupling of Vinyl Boronic Esters using Metallaphotoredox Catalysis",

abstract = "The synthesis of complex alkyl boronic esters via a conjunctive cross‐coupling of vinyl boronic esters with carboxylic acids and aryl iodides is described. The reaction proceeds under mild metallaphotoredox conditions and involves an unprecedented decarboxylative radical addition/cross‐coupling cascade of vinyl boronic esters. Excellent functional group tolerance is displayed, and application of a range of carboxylic acids, namely secondary α‐amino acids, and aryl iodides provides efficient access to highly functionalized alkyl boronic esters. The decarboxylative conjunctive cross‐coupling was also applied to the synthesis of sedum alkaloids.",

keywords = "metallaphotoredox catalysis, decarboxylative crosscoupling, conjunctive cross-coupling, alkyl boronic esters, carboxylic acids",

author = "Mega, \{Riccardo S.\} and Duong, \{Vincent K.\} and Adam Noble and Aggarwal, \{Varinder Kumar\}",

year = "2020",

month = mar,

day = "9",

doi = "10.1002/anie.201916340",

language = "English",

volume = "59",

pages = "4375--4379",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley \& Sons, Ltd.",

number = "11",

}

TY - JOUR

T1 - Decarboxylative Conjunctive Cross-coupling of Vinyl Boronic Esters using Metallaphotoredox Catalysis

AU - Mega, Riccardo S.

AU - Duong, Vincent K.

AU - Noble, Adam

AU - Aggarwal, Varinder Kumar

PY - 2020/3/9

Y1 - 2020/3/9

N2 - The synthesis of complex alkyl boronic esters via a conjunctive cross‐coupling of vinyl boronic esters with carboxylic acids and aryl iodides is described. The reaction proceeds under mild metallaphotoredox conditions and involves an unprecedented decarboxylative radical addition/cross‐coupling cascade of vinyl boronic esters. Excellent functional group tolerance is displayed, and application of a range of carboxylic acids, namely secondary α‐amino acids, and aryl iodides provides efficient access to highly functionalized alkyl boronic esters. The decarboxylative conjunctive cross‐coupling was also applied to the synthesis of sedum alkaloids.

AB - The synthesis of complex alkyl boronic esters via a conjunctive cross‐coupling of vinyl boronic esters with carboxylic acids and aryl iodides is described. The reaction proceeds under mild metallaphotoredox conditions and involves an unprecedented decarboxylative radical addition/cross‐coupling cascade of vinyl boronic esters. Excellent functional group tolerance is displayed, and application of a range of carboxylic acids, namely secondary α‐amino acids, and aryl iodides provides efficient access to highly functionalized alkyl boronic esters. The decarboxylative conjunctive cross‐coupling was also applied to the synthesis of sedum alkaloids.

KW - metallaphotoredox catalysis

KW - decarboxylative crosscoupling

KW - conjunctive cross-coupling

KW - alkyl boronic esters

KW - carboxylic acids

U2 - 10.1002/anie.201916340

DO - 10.1002/anie.201916340

M3 - Article (Academic Journal)

C2 - 31909870

SN - 1433-7851

VL - 59

SP - 4375

EP - 4379

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 11

ER -

Decarboxylative Conjunctive Cross-coupling of Vinyl Boronic Esters using Metallaphotoredox Catalysis

Abstract

Research Groups and Themes

Keywords

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Projects

FRESCO: Efficient, Flexible Synthesis of Molecules with Tailored Shapes: from Photoswitchable Helices to anti-Cancer Compounds

Student theses

Decarboxylative Radical Additions to Vinyl Boronic Esters

Cite this