TY - JOUR
T1 - Preparation of functionalized 3,4-pyridynes via 2-magnesiated diaryl sulfonates
AU - Lin, Wenwei
AU - Chen, Ling
AU - Knochel, Paul
N1 - Funding Information:
We thank the Fonds der Chemischen Industrie, the Deutsche Forschungsgemeinschaft (DFG) and Merck Research Laboratories (MSD) for financial support. We also thank Chemetall GmbH (Frankfurt) and BASF AG (Ludwigshafen) for the generous gift of chemicals.
Copyright:
Copyright 2008 Elsevier B.V., All rights reserved.
PY - 2007/3/26
Y1 - 2007/3/26
N2 - The preparation of functionalized 3,4-pyridynes of type 1 as highly reactive intermediates has been achieved by the controlled elimination of readily generated 2-magnesiated diaryl sulfonates of type 2 obtained by a low temperature I/Mg- or Br/Mg-exchange starting from the corresponding halides of type 3. After trapping with furan, moderate to good yields of the desired functionalized cycloadducts of type 4 are obtained. The addition of a magnesium arylthiolate or magnesium phenylselenide to 3,4-pyridyne followed by quenching with an electrophile is also described.
AB - The preparation of functionalized 3,4-pyridynes of type 1 as highly reactive intermediates has been achieved by the controlled elimination of readily generated 2-magnesiated diaryl sulfonates of type 2 obtained by a low temperature I/Mg- or Br/Mg-exchange starting from the corresponding halides of type 3. After trapping with furan, moderate to good yields of the desired functionalized cycloadducts of type 4 are obtained. The addition of a magnesium arylthiolate or magnesium phenylselenide to 3,4-pyridyne followed by quenching with an electrophile is also described.
KW - Cycloaddition
KW - Functionalized 3,4-pyridyne
KW - Functionalized organomagnesium reagents
KW - Halogen-magnesium exchange
KW - Magnesium
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U2 - 10.1016/j.tet.2007.01.027
DO - 10.1016/j.tet.2007.01.027
M3 - Article
AN - SCOPUS:33847036007
VL - 63
SP - 2787
EP - 2797
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 13
ER -