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Regioselectivity in the Intramolecular Heck Reaction of a Series of Cyclic Sulfonamides: An Experimental and Computational Study
Author(s) -
Geoghegan Kimberly,
Evans Paul,
Rozas Isabel,
Alkorta Ibon
Publication year - 2012
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.201201359
Subject(s) - regioselectivity , intramolecular force , chemistry , alkene , ring (chemistry) , computational chemistry , stereochemistry , organic chemistry , catalysis
Regioselectivity in the intramolecular Heck reaction of a series of N ‐sulfonyl‐2,5‐dihydro‐3‐substituted pyrroles was studied. These substrates are unbiased in terms of the formed ring size of the new heterocycle. Results indicate that high levels of regioselectivity are observed under a range of conditions, and that there is an underlying propensity for carbon–carbon bond formation at the most hindered end of the alkene. For two examples (3‐Me and 3‐ t Bu), DFT calculations were performed and indicate that in both cases, the modelled transition state for carbopalladation is energetically lower for the experimentally preferred isomer.