Deprotonative cadmation of functionalized aromatics.
نویسندگان
چکیده
This communication describes the deproto-metalation of a large range of aromatics including heterocycles using a newly developed lithium-cadmium base; the reaction proceeds at room temperature with an excellent chemoselectivity and efficiency, and proved to be regioselective in most cases.
منابع مشابه
[A novel deprotonative functionalization of aromatics with phosphazene base].
A novel type of deprotonative functionalization of aromatics was accomplished with a phosphazene base (t-Bu-P4 base). For various nitrogen heteroaromatics and benzene derivatives, deprotonative 1,2-additions proceeded with the t-Bu-P4 base and ZnI(2) as an additive in the presence of carbonyl compounds. The t-Bu-P4 base has both extremely strong Brønsted basicity and less nucleophilicity due to...
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[1,2,3]Triazolo[1,5-a]pyridine and 3-substituted derivatives were regioselectively metalated at the 7 position using either Bu3MgLi or (TMP)3CdLi, the former at -10 degrees C and the latter at room temperature. The lithium arylmagnesates (R = H, Me, Ph) proved to react with iodine (34-75%) or 3,4,5-trimethoxybenzaldehyde (32-51%). Attempts to obtain the cross-coupling products using 2-bromopyri...
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A novel type of deprotonative arylation of nucleophiles was conducted using Et(3)SiH/cat. t-Bu-P4 and the powerful S(N)Ar reactions of aryl fluorides were accomplished using alcohols and malonates as nucleophiles.
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Deprotonation of benzoxazole, benzothiazole, benzo[b]thiophene, benzo[b]furan, N-Boc-protected indole and pyrrole, and N-phenylpyrazole using an in situ mixture of ZnCl(2).TMEDA (0.5 equiv) and lithium 2,2,6,6-tetramethylpiperidide (1.5 equiv) in THF at room temperature is described. The reaction was evidenced by trapping with iodine, regioselectively giving the expected functionalized derivati...
متن کاملPalladium-Catalyzed α-Arylation of Benzylic Phosphonates
A new synthetic route to access diarylmethyl phosphonates is presented. The transformation enables the introduction of aromatic groups on benzylic phosphonates via a deprotonative cross-coupling process (DCCP). The Pd(OAc)2/CataCXium A-based catalyst afforded a reaction between benzyl diisopropyl phosphonate derivatives and aryl bromides in good to excellent isolated yields (64-92%).
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ورودعنوان ژورنال:
- Chemical communications
دوره 42 شماره
صفحات -
تاریخ انتشار 2008