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Regiospecific Reductive Elimination from Diaryliodonium Salts
Author(s) -
Wang Bijia,
Graskemper Joseph W.,
Qin Linlin,
DiMagno Stephen G.
Publication year - 2010
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.201000695
Subject(s) - steric effects , substituent , chemistry , reductive elimination , transition metal , cyclophane , iodine , photochemistry , combinatorial chemistry , stereochemistry , crystallography , organic chemistry , crystal structure , catalysis
Out‐of‐plane steric bulk furnished by a cyclophane substituent on iodine(III) strongly destabilizes the transition state in the reductive elimination from diaryliodonium salts and leads to regiochemical control (dubbed SECURE), as is demonstrated by computational and experimental studies. This approach should be general for high‐valent main‐group and transition metal ions. X=N 3 , OAc, PhO, CF 3 CH 2 O, SCN, PhS.