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Vaulted Biaryls in Catalysis: A Structure–Activity Relationship Guided Tour of the Immanent Domain of the VANOL Ligand
Author(s) -
Guan Yong,
Ding Zhensheng,
Wulff William D.
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201302451
Subject(s) - ligand (biochemistry) , chemistry , catalysis , substrate (aquarium) , naphthalene , molecule , stereochemistry , oxygen atom , crystallography , organic chemistry , receptor , biochemistry , oceanography , geology
The active site in the BOROX catalyst is a chiral polyborate anion (boroxinate) that is assembled in situ from three equivalents of B(OPh) 3 and one of the VANOL ligand by a molecule of substrate. The substrates are bound to the boroxinate by H bonds to oxygen atoms O1–O3. The effects of introducing substituents at each position of the naphthalene core of the VANOL ligand are systematically investigated in an aziridination reaction. Substituents in the 4,4′‐ and 8,8′‐positions have a negative effect on catalyst performance, whereas, substituents in the 7‐ and 7′‐positions have the biggest impact in a positive direction.