期刊
SYNTHESIS-STUTTGART
卷 51, 期 11, 页码 2278-2286出版社
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0037-1610877
关键词
sulfonyl fluorides; fluorosulfates; directed; ortho; -metalation; SuFEx; orthogonal reactivity; in situ trap; lithium amides; anionic thia-Fries rearrangement
资金
- SONATA BIS program of the Narodowe Centrum Nauki (National Science Centre, Poland, NCN) [DEC-2013/10/E/ST5/00030]
Studies on directed ortho -metalation (DoM) of arenesulfonyl fluorides (ArSO (2) F) with in situ electrophile trapping are presented. Under optimized conditions (LDA, THF, -78 degrees C), a series of model substrates was mono- and difunctionalized with trimethylsilyl chloride in good yields. The synthetic results reveal powerful directing character of the SO (2) F group, being ahead of bromine and methoxy substituents. Under the same metalation conditions, aryl fluorosulfates (ArOSO (2) F) display fragmentation to arynes and migration of the SO (2) F group to the ortho position (anionic thia-Fries rearrangement).
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