Silicon–nitrogen bond formation via dealkynative coupling of amines with bis(trimethylsilyl)acetylene mediated by KHMDS

Abstract

The catalytic synthesis of silylamines mediated by s- and p-block catalysts is largely underdeveloped. Herein, commercially available potassium bis(trimethylsilyl)amide serves as an efficient alternative to transition metal complexes. N–H/Si–C dealkynative...

Reactions of 5-(Trialkyl)silylpent-1-en-4-yn-3-ones with Hydrazines: Original Synthetic Routes to Luminescent Substances Containing Azole Motifs

“…At the same time, penta-coordinated silicon structure C is formed at the first stage. Structures, similar to C, have already been claimed 42 for the decomposition mechanism of a Si-C sp bond influenced by RNHion. As a result of the further decomposition of C, followed by proton transfer involving solvent or reagent 2c, the formation of enynone 1b and 1-phenyl-2-(trimethylsilyl)hydrazine D happens.…”

“…Calcd for C 23 H 25 N 3 O 2 SSi: C, 63. 42;H,5.78;N,9.65;S,7.36;Si,6.45. Found: C,63.47;H,5.78;N,9.81;S,7.27;Si,6.69.…”

Access to germasiloxanes and alkynylgermanes mediated by earth-abundant species

“…Thus, except for bulky triisopropyl(ethynyl)germane (4c; 53%), the reaction smoothly proceeded with remaining alkynylgermanes in good to excellent yields (72-95%). Guided by our previous studies 45,48,49 , we explored the versatility of our dealkynative coupling of 4a (or 4d) employing a representative set of terminal alkynes (Fig. 4).…”

“…Thus, we sought the method leading to versatile germanium compounds that blends the high selectivity of TM-mediated approaches with the practicality of a base-promoted protocol. Based on our recent success in activating silylacetylenes under sustainable catalysis [45][46][47][48][49] , we reasoned that an appropriate catalytic manifold could provide an efficient platform to generate diversified libraries of organogermanes. In this…”

Base-catalyzed addition of silylacetylenes to ketones: a route to protected tertiary propargyl alcohols

“…[27][28][29][30][31][32][33][34][35][36][37] The application of Earth-abundant species as catalysts have gained recent significant attention in organic chemistry. [38][39][40][41][42][43][44][45][46][47][48][49] Considering our recent success in activating organometalloids under sustainable catalysis, [50][51][52][53][54][55][56] we reasoned that an appropriate catalytic manifold could provide an efficient platform to generate diversified libraries of protected propargyl alcohols. To address the limitations of previously mentioned methods, herein we report the KHMDS-catalyzed addition of silylacetylenes to ketones.…”