Transition-metal- or oxidant-promoted deconstructive functionalizations of noncyclic carbon–nitrogen bonds are well established, usually only leaving one moiety functionalized toward the final product. In contrast, concomitant C- and N-functionalizations via the unstrained C(sp³)–N bond under metal- and oxidant-free conditions are very rare, which would favorably confer versatility and product diversity. Disclosed herein is the first difluorocarbene-induced deconstructive functionalizations embodying successive C(sp³)–N bond cleavage of cyclic amines and synchronous functionalization of both constituent atoms which would be preserved in the eventual molecular outputs under transition-metal-free and oxidant-free conditions. Correspondent access to deuterated formamides with ample isotopic incorporation was demonstrated by a switch to heavy water which is conceivably useful in pharmaceutical sciences. The current strategy remarkably administers a very convenient, operationally simple and novel method toward molecular diversity from readily available starting materials. Therefore, we project that these findings would be of broad interest to research endeavors encompassing fluorine chemistry, carbene chemistry, C–N bond activation, as well as medicinal chemistry.

中文翻译：

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由二氟卡宾进行的无应变碳氮裂解的解构功能化

过渡金属或氧化剂促进的非环状碳氮键解构官能化作用已得到很好的确立，通常只剩下一个对最终产物官能化的部分。相反，在无金属和无氧化剂的条件下，通过未应变的C（sp ³）–N键伴随的C和N官能化非常罕见，这有利于赋予通用性和产品多样性。本文公开的是首个由二氟卡宾诱导的解构功能化，体现为连续的C（sp ³）–环胺的N键裂解和两个组成原子的同步官能化，这些最终原子将在无过渡金属和无氧化剂的条件下保留下来。通过改用重水可以证明与相应的氘化甲酰胺有足够的同位素结合，这在制药科学中很有用。当前的策略显着地管理了一种非常方便，操作简单且新颖的方法来从容易获得的起始原料中获得分子多样性。因此，我们预计这些发现将对包括氟化学，卡宾化学，C–N键活化以及药物化学在内的研究工作产生广泛的兴趣。