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(sp 3 )–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(sp 3 )–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.

CF 3 -containing diborylated compounds were successfully prepared from readily available CF 3 bearing 1,3-enynes, without fluorine elimination, and subsequently, several useful fluorine-containing molecules were synthesized. These transformations exhibit a high degree of regio-, stereo-, and chemoselectivity, affording CF 3 containing E-1,3-, Z-1,3and Z-1,4-diborylated olefins. Control experiments and density functional theory calculations provide explanations for the observed selectivities.

Manipulation of the alkyl chain branching point has emerged as an effective strategy to enhance the performance of conjugated polymers in organic electronic devices. In this work, a highly efficient...

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