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First Comprehensive Investigation of Suzuki Couplings of Alkenyl Nonaflates with Aryl and Alkenyl Boronic Acid Derivatives by Using Classical Conditions and Microwave Heating
Author(s) -
Högermeier Jens,
Reißig HansUlrich
Publication year - 2007
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.200601394
Subject(s) - bicyclic molecule , suzuki reaction , aryl , chemistry , boronic acid , pyran , furanose , microwave irradiation , combinatorial chemistry , stereoselectivity , organic chemistry , ring (chemistry) , catalysis , alkyl
Alkenyl nonaflates (nonafluorobutanesulfonates) are excellent substrates in a variety of palladium‐catalysed coupling reactions. We herein demonstrate that bicyclic nonaflates generated from 8‐heterobicyclo[3.2.1]octan‐3‐one derivatives can be coupled with aryl or alkenyl boronic acids in a very efficient manner. The resulting densely functionalised bicyclic skeletons are highly suitable for further synthetic elaboration. The thermal Suzuki couplings provided the expected products in moderate to good yields. Microwave (MW) irradiation dramatically shortened reaction times and gave superior results. Bisboronic ester 19 was also coupled with bicyclic nonaflates, for example, with 14 , and double Suzuki‐coupling products, such as 22 , were isolated in good yields. We demonstrated the great synthetic potential of aryl‐substituted 8‐heterobicyclo[3.2.1]octene derivatives, such as 15 , by the stereoselective conversion of this compound into highly substituted furanose 31 or substituted pyran derivative 33 , which were obtained in short and efficient reaction sequences.