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A cascade process for directly converting nitriles (RCN) to cyanamides (RNHCN) via SO2F2-activated Tiemann rearrangement.
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2019-08-08 , DOI: 10.1039/c9ob01547g
Guofu Zhang 1 , Yiyong Zhao 1 , Chengrong Ding 1
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2019-08-08 , DOI: 10.1039/c9ob01547g
Guofu Zhang 1 , Yiyong Zhao 1 , Chengrong Ding 1
Affiliation
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A simple, mild and practical process for the direct conversion of nitriles to cyanamides was newly discovered and exhibited a wide substrate scope as well as great functional group-tolerability (36 examples). In this efficient strategy, the in situ generated amidoximes obtained from the reaction of nitriles with hydroxylamine subsequently underwent Tiemann rearrangement, producing the corresponding cyanamides with great isolated yields under SO2F2. Additionally, the control experiments reportedly shed light on the tentative mechanism involved in the formation and elimination of the key intermediate: a sulfonyl ester.
中文翻译:
通过SO2F2激活的Tiemann重排将腈(RCN)直接转化为氰胺(RNHCN)的级联过程。
最近发现了一种简单,温和且实用的腈直接转化为氰胺的方法,该方法具有广泛的底物范围和强大的官能团耐受性(36个实例)。在这种有效的策略中,从腈与羟胺的反应中获得的原位生成的氨基肟,随后进行了Tiemann重排,在SO2F2下以高分离产率生产了相应的氰酰胺。另外,据报道,对照实验阐明了参与形成和消除关键中间体磺酰酯的初步机制。
更新日期:2019-08-21
中文翻译:
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通过SO2F2激活的Tiemann重排将腈(RCN)直接转化为氰胺(RNHCN)的级联过程。
最近发现了一种简单,温和且实用的腈直接转化为氰胺的方法,该方法具有广泛的底物范围和强大的官能团耐受性(36个实例)。在这种有效的策略中,从腈与羟胺的反应中获得的原位生成的氨基肟,随后进行了Tiemann重排,在SO2F2下以高分离产率生产了相应的氰酰胺。另外,据报道,对照实验阐明了参与形成和消除关键中间体磺酰酯的初步机制。