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Competing Regiochemical Pathways in the Heck Arylation of 1,2‐Dihydronaphthalene
Author(s) -
Maeda Kenji,
Farrington Edward J.,
Galardon Erwan,
John Benjamin D.,
Brown John M.
Publication year - 2002
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/1615-4169(200201)344:1<104::aid-adsc104>3.0.co;2-v
Subject(s) - chemistry , regioselectivity , aryl , heck reaction , ring (chemistry) , medicinal chemistry , organic chemistry , catalysis , alkyl
The Heck reaction of aryl iodides with 1,2‐dihydronaphthalene has been examined. Two separate reaction pathways are observed under all the conditions tried. Arylation adjacent to the aromatic ring leads to a subsequent double bond shift such that the product is a 1‐aryl‐1,2‐dihydronaphthalene. The alternative regiochemistry leads to production of the corresponding 3‐aryl‐1,2‐dihydronaphthalene, and labelling studies with specifically deuterated alkenes demonstrate that this is most likely to be the result of a trans Pd‐H elimination pathway. The ratio always varies between 75 : 25 in favour of the 3‐aryl product (Jeffery conditions) to 70 : 30 in favour of the 1‐aryl product.