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Weak Arene C[BOND]H⋅⋅⋅O Hydrogen Bonding in Palladium-Catalyzed Arylation and Vinylation of Lactones

Authors

  • Dr. Zhiyan Huang,

    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore)
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  • Dr. Zuliang Chen,

    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore)
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  • Li Hui Lim,

    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore)
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  • Gia Chuong Phan Quang,

    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore)
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  • Prof. Dr. Hajime Hirao,

    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore)
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  • Prof. Dr. Jianrong (Steve) Zhou

    Corresponding author
    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore)
    • Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore)

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  • We thank the Singapore National Research Foundation (NRF-RF2008-10) and Nanyang Technological University for financial support, and Johnson-Matthey for a gift of palladium.

Abstract

original image

Weak force in action: In the title reaction, the palladium catalyst (see figure, left) uses weak CH⋅⋅⋅O hydrogen bonding to control the absolute configuration of the new stereocenter. A similar palladium catalyst (right) used conventional NH⋅⋅⋅O hydrogen bonding to guide stereoselection.

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