- Electrochemical Reductive Smiles Rearrangement for C-N Bond Formation
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A conceptually new and synthetically valuable radical Smiles rearrangement reaction is reported under undivided electrolytic conditions. This protocol employs an entirely new strategy for the electrochemical radical Smiles rearrangement. Remarkably, an amidyl radical generated from the cleavage of the N-O bond under reductive electrolytic conditions plays a crucial role in this transformation. Various hydroxylamine derivatives bearing different substituents are suitable in this electrochemical transformation, furnishing the corresponding amides in up to 86% yield.
- Chang, Xihao,Zhang, Qinglin,Guo, Chang
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- A diversity-oriented synthesis of bioactive benzanilides via a regioselective C(sp2)-H hydroxylation strategy
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A diversity-oriented synthesis of bioactive benzanilides via C(sp2)-H hydroxylation has been studied. Different regioselectivity was observed with Ru(ii) and Pd(ii) catalysts. The reaction demonstrates excellent regioselectivity, good tolerance
- Sun, Yong-Hui,Sun, Tian-Yu,Wu, Yun-Dong,Zhang, Xinhao,Rao, Yu
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p. 2229 - 2238
(2016/03/05)
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- Intramolecular metal-free oxidative aryl-aryl coupling: An unusual hypervalent-iodine-mediated rearrangement of 2-substituted n-phenylbenzamides
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Hypervalent-iodine-mediated oxidative coupling of the two aryl groups in either 2-acylamino-N-phenyl-benzamides or 2-hydroxy-N-phenylbenzamides, with concomitant insertion of the ortho-substituted N or O atom into the tether, has been described for the first time. This unusual metal-free rearrangement reaction involves an oxidative C(sp2)?C(sp2) aryl-aryl bond formation, cleavage of a C(sp2)?C(O) bond, and a lactamization/lactonization. Furthermore, unsymmetrical diaryl compounds can be easily obtained by removing the tether within the cyclized product.
- Shang, Siyun,Zhang-Negrerie, Daisy,Du, Yunfei,Zhao, Kang
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supporting information
p. 6216 - 6219
(2014/06/23)
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