A Unique Approach to Metal‐Induced Bergman Cyclization: Long‐Range Enediyne Activation by Ligand‐to‐Metal Charge Transfer | Zendy

Bhattacharyya Sibaprasad | Zendy; Pink Maren | Zendy; Baik  MuHyun | Zendy; Zaleski Jeffrey M. | Zendy

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A Unique Approach to Metal‐Induced Bergman Cyclization: Long‐Range Enediyne Activation by Ligand‐to‐Metal Charge Transfer

Author(s) -

Bhattacharyya Sibaprasad,

Pink Maren,

Baik MuHyun,

Zaleski Jeffrey M.

Publication year - 2005

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.200461825

Subject(s) - enediyne , metal , charge (physics) , ligand (biochemistry) , range (aeronautics) , chemistry , materials science , physics , stereochemistry , quantum mechanics , composite material , organic chemistry , receptor , biochemistry

Dramatic differences are found in the temperatures at which Bergman cyclizations occur when Mo IV –enedithiolate–enediyne complexes are used (see scheme; S: yellow, Mo: red), and this can be directly attributed to a long‐range electronic polarization effect of the metal center. Ligand‐to‐metal charge transfer within the C 2 S 4 substructure and differential charge repulsion in the transition state lead to a lowering of the barrier to cyclization.

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