Site-Selective 1,2-Dicarbofunctionalization of Vinyl Boronates through Dual Catalysis

doi:10.1002/anie.201916279

. 2020 Mar 9;59(11):4370-4374.

doi: 10.1002/anie.201916279. Epub 2020 Feb 3.

Site-Selective 1,2-Dicarbofunctionalization of Vinyl Boronates through Dual Catalysis

Shang-Zheng Sun^{1

2}, Yaya Duan¹, Riccardo S Mega¹, Rosie J Somerville^{1

2}, Ruben Martin^{1

3}

Affiliations

¹ Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007, Tarragona, Spain.
² Universitat Rovira i Virgili, Departament de Química Analítica i Química Orgànica, c/Marcel lí Domingo, 1, 43007, Tarragona, Spain.
³ Catalan Institution for Research and Advanced Studies (ICREA), Passeig Lluïs Companys, 23, 08010, Barcelona, Spain.

PMID: 31910307
DOI: 10.1002/anie.201916279

Site-Selective 1,2-Dicarbofunctionalization of Vinyl Boronates through Dual Catalysis

Shang-Zheng Sun et al. Angew Chem Int Ed Engl. 2020.

. 2020 Mar 9;59(11):4370-4374.

doi: 10.1002/anie.201916279. Epub 2020 Feb 3.

Authors

Shang-Zheng Sun^{1

2}, Yaya Duan¹, Riccardo S Mega¹, Rosie J Somerville^{1

2}, Ruben Martin^{1

3}

Affiliations

¹ Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007, Tarragona, Spain.
² Universitat Rovira i Virgili, Departament de Química Analítica i Química Orgànica, c/Marcel lí Domingo, 1, 43007, Tarragona, Spain.
³ Catalan Institution for Research and Advanced Studies (ICREA), Passeig Lluïs Companys, 23, 08010, Barcelona, Spain.

PMID: 31910307
DOI: 10.1002/anie.201916279

Abstract

A modular, site-selective 1,2-dicarbofunctionalization of vinyl boronates with organic halides through dual catalysis is described. This reaction proceeds under mild conditions and is characterized by excellent chemo- and regioselectivity. It thus represents a complementary new technique for preparing densely functionalized alkyl boron architectures from simple and accessible precursors.

Keywords: Ni; dicarbofunctionalization; dual catalysis; homogeneous catalysis; radical reactions.

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References

1. None
1. Boronic Acids: Preparation and Applications in Organic Synthesis Medicine and Materials (Ed.: D. G. Hall), Wiley-VCH, Weinheim, 2011.
1. An elegant platform based on the utilization of well-defined organozinc reagents: J. Schmidt, J. Choi, A. T. Liu, M. Slusarczyk, G. C. Fu, Science 2016, 354, 1265.
1. Selected reviews for hydroboration:
1. H. C. Brown, Hydroboration, Benjamin/Cummings, New York, 1980;

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AEI/PGC2018-096839-B-100/MICIU

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[1] None

[2] None

[3] Boronic Acids: Preparation and Applications in Organic Synthesis Medicine and Materials (Ed.: D. G. Hall), Wiley-VCH, Weinheim, 2011.

[4] Boronic Acids: Preparation and Applications in Organic Synthesis Medicine and Materials (Ed.: D. G. Hall), Wiley-VCH, Weinheim, 2011.

[5] An elegant platform based on the utilization of well-defined organozinc reagents: J. Schmidt, J. Choi, A. T. Liu, M. Slusarczyk, G. C. Fu, Science 2016, 354, 1265.

[6] An elegant platform based on the utilization of well-defined organozinc reagents: J. Schmidt, J. Choi, A. T. Liu, M. Slusarczyk, G. C. Fu, Science 2016, 354, 1265.

[7] Selected reviews for hydroboration:

[8] Selected reviews for hydroboration:

[9] H. C. Brown, Hydroboration, Benjamin/Cummings, New York, 1980;

[10] H. C. Brown, Hydroboration, Benjamin/Cummings, New York, 1980;

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Site-Selective 1,2-Dicarbofunctionalization of Vinyl Boronates through Dual Catalysis

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Site-Selective 1,2-Dicarbofunctionalization of Vinyl Boronates through Dual Catalysis

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