Facile synthesis of tribenzosilepins from terphenyls and dihydrosilanes by electrophilic double silylation

Dong, Yafang; Sekine, Kohei; Kuninobu, Yoichiro

doi:10.1039/d1cc02326h

Cited by 8 publications

(2 citation statements)

References 48 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In 2021, the research group of Kuninobu reported a double sila‐Friedel‐Crafts reaction of amino‐group‐containing terphenyls 81 and dihydrosilanes 80 using the FLP of B(C 6 F 5 ) 3 and 2,6‐lutidine, affording a series of a seven‐membered heterocyclic tribenzosilepin derivatives 82 in of 24–93 % yield (Scheme 18). [27b] …”

Section: Dual Catalysis Of Boron and Organocatalystmentioning

confidence: 99%

Dual Catalysis Involving Organoboron Compounds

Liu

2022

Eur J Org Chem

View full text Add to dashboard Cite

show abstract

Section: Dual Catalysis Of Boron and Organocatalystmentioning

confidence: 99%

Dual Catalysis Involving Organoboron Compounds

Liu

2022

Eur J Org Chem

View full text Add to dashboard Cite

show abstract

“…Explicitly, the silicon analogues of medicinal molecules exhibit superior pharmacological action . Because of the growing prevalence of the organosilicon skeleton, leading synthetic organic chemists have been spurred to seek out efficient methods to synthesize intricate organosilicon scaffolds . Hydrosilylation of olefins is a very useful method to install a single silyl unit on an olefinic skeleton .…”

Section: Introductionmentioning

confidence: 99%

Silylarylation of Alkenes via meta-Selective C–H Activation of Arenes under Ruthenium/Iron Cooperative Catalysis: Mechanistic Insights from Combined Experimental and Computational Studies

Neogi,

Bhunya,

Kumar Ghosh

et al. 2024

ACS Catal.

View full text Add to dashboard Cite

Organosilicons are privileged skeletons in the domains of pharmaceutical chemistry, organic synthesis, and materials science. Hence, investigating catalytic techniques for the synthesis of organosilicon compounds has received a great deal of emphasis. Carbosilylation of alkenes is an efficient technique to introduce diverse molecular architectures containing silicon into the chemical space. However, organohalides and pseudohalides are prerequisites for most of the existing carbosilylation protocols. On the other hand, the utilization of C−H activation has been sowing the seeds for the successful development of intricate molecular scaffolds. In this regard, the synthetic accessibility of complexed organosilicon derivatives by the carbosilylation of alkenes through the catalytic meta-C−H activation approach has remained intangible. Herein, we present a three-component strategy of arylsilylation of olefins with (het)arenes and silanes by integrating the iron-catalyzed silyl radical generation, coupled to intrinsic reactivity of the silyl radical with an alkene, to the rutheniumcatalyzed meta-C−H functionalization of (het)arene, leading to the targeted cross-coupled carbosilylated product. In addition, theoretical investigations with state-of-the-art dispersion corrected density functional theory at B3PW91-D3/Def2TZVP/ CPCM(PhCF 3 ) shed intriguing insights on selectivity and the probable mechanistic pathway of the underexplored cooperative 3d/4d transition metal catalysis, such as the formation of the silyl radical and its addition to the alkene catalyzed by iron, followed by meta-selective C−H functionalization of the ruthenium bound arene, furnishing C4 substituted (het)arene functionalized organosilicon compounds.

show abstract

Gold‐Catalyzed Synthesis of 5H‐Benzo[b]indeno[2,1‐d]silines by Insertion of Vinyl Carbocations into the Si−H Bond

Sekine,

Fuji,

Kawashima

et al. 2024

Chemistry A European J

View full text Add to dashboard Cite

We have developed a gold‐catalyzed cascade reaction of aryldiynes bearing a hydrosilyl group to afford a variety of unexplored 5H‐benzo[b]indeno[2,1‐d]silines. The reaction system is applicable to the synthesis of bidirectionally π‐extended silacycles from tetra(alkynyl)aryl compounds. Computational studies suggest that 5H‐benzo[b]indeno[2,1‐d]silines are formed via the insertion of a vinyl carbocation intermediate into the Si–H bond.

show abstract

Facile synthesis of tribenzosilepins from terphenyls and dihydrosilanes by electrophilic double silylation

Abstract: Tribenzosilepins were synthesized from terphenyls and dihydrosilanes using a facile approach using a double sila-Friedel–Crafts reaction. Several silepin derivatives were obtained in moderate to high yield. The reaction system was...

Cited by 8 publications

References 48 publications

Dual Catalysis Involving Organoboron Compounds

Dual Catalysis Involving Organoboron Compounds

Silylarylation of Alkenes via meta-Selective C–H Activation of Arenes under Ruthenium/Iron Cooperative Catalysis: Mechanistic Insights from Combined Experimental and Computational Studies

Gold‐Catalyzed Synthesis of 5H‐Benzo[b]indeno[2,1‐d]silines by Insertion of Vinyl Carbocations into the Si−H Bond

Contact Info

Product

Resources

About