Details

Autor(en) / Beteiligte

• Ma, Xingxing
• Su, Jianke
• Zhang, Xingang
• Song, Qiuling

Titel

Chlorodifluoromethane as a C1 Synthon in the Assembly of N-Containing Compounds

Ist Teil von

• iScience, 2019-09, Vol.19, p.1-13

Ort / Verlag

United States: Elsevier Inc

Erscheinungsjahr

2019

Link zum Volltext

Quelle

EZB-FREE-00999 freely available EZB journals

Beschreibungen/Notizen

• The development of C1 synthons to afford the products that add one extra carbon has become an important research theme in the past decade, and significant progress has been achieved with CO2, CO, HCOOH, and others as C1 units. Despite the great advance, the search for new C1 synthons that display unique reactivity, complement to the current C1 sources, and add more value to C1 chemistry is still desirable. Herein, we report a quadruple cleavage of chlorodifluoromethane to yield a C1 source, which was successfully employed in the construction of various N-containing compounds especially with pharmaceutical molecules under mild conditions. This strategy provides a useful method for late-stage modification of pharmaceutical compounds. Four bonds in ClCF2H were orderly cleaved under basic conditions in the absence of transition metals. Preliminary mechanistic studies revealed that (E)-N-phenylformimidoyl fluoride intermediate is involved in this process by in situ1H NMR studies and control experiments. [Display omitted] •Quadruple cleavage of ClCF2H to afford a C1 synthon•The cleavage of two stable C(sp3)-F bonds in aliphatic gem-difluoroalkanes•Enrich C1 chemistry, green chemistry, and fluorine chemistry•Various N-containing compounds were afforded via different role of ClCF2H Catalysis; Organic Chemistry; Organic Synthesis