ISSN:
0947-3440
Keywords:
Heck reaction, intramolecular
;
Isochromane
;
Palladium
;
Heterocycles
;
High-pressure chemistry
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The iodoarenes 9 and 10, bearing (E)- and (Z)-alkene moieties, respectively, easily prepared by alkylation of the corresponding alcohols 7a-c and 8a-c with 2 iodobenzyl iodide, undergo intramolecular Heck reactions to give the isochromanes 12-15a-c in good yields. The selectivity of the reaction depends on the size of the substituent R in 9 and 10; increasing bulkiness of R leads to a decrease in diastereoselectivity and an increase in regioselectivity. High-pressure experiments confirm the proposed mechanism and show that bromoarenes such as 11, which tend to be unreactive at ambient pressure, give good results when the cyclisation is performed under high pressure.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199719970516
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