Ring Expansion of Silacyclobutanes with Allenoates to Selectively Construct 2- or 3-(E)-Enoate-Substituted Silacyclohexenes

Transition-metal-catalyzed sila-cycloaddition has been a promising tool for accessing silacarbocycle derivatives, but the approach has been limited to a selection of well-defined sila-synthons. Herein, we demonstrate the potential of chlorosilanes, which are industrial feedstock chemicals, for this type of reaction under reductive nickel catalysis. This work extends the scope of reductive coupling from carbocycle to silacarbocycle synthesis and from single C-Si bond formation to sila-cycloaddition reactions. The reaction proceeds under mild conditions and shows good substrate scope and functionality tolerance, and it offers new access to silacyclopent-3-enes and spiro silacarbocycles. The optical properties of several spiro dithienosiloles as well as structural variations of the products are demonstrated.

Nickel-Catalyzed Reductive [4 + 1] Sila-Cycloaddition of 1,3-Dienes with Dichlorosilanes.

Despite growing progress in the construction of silazanes, the catalytic asymmetric synthesis of silicon-stereogenic silazanes is significantly less explored and remains a considerable challenge. Herein, we report a highly enantioselective synthesis of silicon-stereogenic silazanes via catalytic dehydrogenative coupling of dihydrosilanes with anilines. The reaction readily produces a wide range of chiral silazanes and bis-silazanes in excellent yields and stereoselectivities (up to 99% ee). Further utility of this process is demonstrated by the construction of polycarbosilazanes featuring configurational main chain silicon-stereogenic chirality. In addition, the straightforward transformation of the enantioenriched silazanes delivers various chiral silane compounds in a stereospecific fashion, illustrating their potential utilities as synthons for the synthesis of novel silicon-containing functional molecules.

Catalytic Asymmetric Dehydrogenative Si-H/N-H Coupling: Synthesis of Silicon-Stereogenic Silazanes.

Transition-metal-catalyzed intermolecular annulation of silicon reagents with organic molecules is still underdeveloped due to the scarcity of silicon reagent types and their diverse reactivity. Herein, a readily accessible silicon reagent (octamethyl-1,4-dioxacyclohexasilane) has been developed for divergent synthesis of silacycles via time-controlled palladium-catalyzed cascade C-H silacyclization. This protocol enables the rapid and selective transformation of acrylamides into spirosilacycles with different ring sizes, including benzodioxatetrasilecines, benzooxadisilepines, and benzosiloles, in moderate to good yields through a time switch. Notably, the tetrasilane reagent can also be utilized for C-H silacyclization of 2-halo-N-methacryloylbenzamides and 2-iodobiphenyls, leading to diverse fused silacycles. Furthermore, several synthetic transformations of products are achieved. A series of mechanistic studies demonstrate the transformation relationships and possible pathways among ten-, seven-, and five-membered silacycles.

Versatile Tetrasilane for Time-Controlled Palladium-Catalyzed Divergent Synthesis of Silacycles via C-H Activation.

Visible-Light-Induced, Palladium-Catalyzed Annulation of 1,3-Dienes to Construct Vinyl N-Heterocycles.

Small-ring silacycles are important organosilane species in main-group chemistry and have found numerous applications in organic synthesis. 3-Silaazetidine, a unique small silacycle bearing silicon and nitrogen atoms, has not been adequately explored due to the lack of a general synthetic scheme and its sensitivity to air. Here, we describe that 3-silaazetidine can be easily prepared in situ from diverse air-stable precursors (RSO2NHCH2SiR12CH2Cl). 3-Silaazetidine shows excellent functional group tolerance in a palladium-catalyzed ring expansion reaction with terminal alkynes, giving 3-silatetrahydropyridines and diverse silaazacycle derivatives, which are promising ring frameworks for the discovery of Si-containing functional molecules.

3-Silaazetidine: An Unexplored yet Versatile Organosilane Species for Ring Expansion toward Silaazacycles.

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3-Silaazetidine: An Unexplored yet Versatile Organosilane Species for Ring Expansion toward Silaazacycles.