Construction of Silicon-Containing Seven-Membered Rings by Catalytic [4 + 2 + 1] Cycloaddition through Rhodium Silylenoid

Sasaki, Ikuo; Ohmura, Toshimichi; Suginome, Michinori

doi:10.1021/acs.orglett.0c00690

Cited by 21 publications

(8 citation statements)

References 55 publications

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“…Just recently, Ohmura and Suginome extended this rhodium catalysis to a (4+2+1) cycloaddition. 140 Based on the key intermediate, that is the ''rhodium silylenoid'', in the reaction, the authors successfully developed a (4+2+1) cycloaddition of nona-1,3dien-8-yne derivatives 359 and boryl(isopropoxy)silane (356) in the presence of a rhodium catalyst and dppm as ligand (Scheme 119, top). A series of silicon-containing seven-membered rings was obtained (359a-g -360a-g).…”

Section: (2+2+1)-and (4+2+1)cycloadditions Of Multiple-bond Systemsmentioning

confidence: 99%

Activation of the Si–B interelement bond related to catalysis

et al. 2021

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Section: (2+2+1)-and (4+2+1)cycloadditions Of Multiple-bond Systemsmentioning

confidence: 99%

Activation of the Si–B interelement bond related to catalysis

et al. 2021

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“…The construction of strained seven-membered rings containing a bridged biaryl atropisomer is challenging. − Based on the previous achievements in atropisomer construction, a facile approach to construct lactone-bridged biaryl atropisomers 144 from acyoxylated biaryls 143 has been developed . The approach involves a palladium-catalyzed intramolecular diastereoselective Mizoroki–Heck cyclization (Scheme ).…”

Section: Synthetic Applications Of Cyclic Aryliodoniumsmentioning

confidence: 99%

Recent Progress in Cyclic Aryliodonium Chemistry: Syntheses and Applications

et al. 2023

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Hypervalent aryliodoumiums are intensively investigated as arylating agents. They are excellent surrogates to aryl halides, and moreover they exhibit better reactivity, which allows the corresponding arylation reactions to be performed under mild conditions. In the past decades, acyclic aryliodoniums are widely explored as arylation agents. However, the unmet need for acyclic aryliodoniums is the improvement of their notoriously low reaction economy because the coproduced aryl iodides during the arylation are often wasted. Cyclic aryliodoniums have their intrinsic advantage in terms of reaction economy, and they have started to receive considerable attention due to their valuable synthetic applications to initiate cascade reactions, which can enable the construction of complex structures, including polycycles with potential pharmaceutical and functional properties. Here, we are summarizing the recent advances made in the research field of cyclic aryliodoniums, including the nascent design of aryliodonium species and their synthetic applications. First, the general preparation of typical diphenyl iodoniums is described, followed by the construction of heterocyclic iodoniums and monoaryl iodoniums. Then, the initiated arylations coupled with subsequent domino reactions are summarized to construct polycycles. Meanwhile, the advances in cyclic aryliodoniums for building biaryls including axial atropisomers are discussed in a systematic manner. Finally, a very recent advance of cyclic aryliodoniums employed as halogen-bonding organocatalysts is described.

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“…1a) 6,13,[14][15][16][17][18][19][20][21][22][23][24][25][26][27] . Among those elegant silicon-bridged biaryls, only limited examples possess six-or seven-membered silicon-bridged pconjugated scaffolds [28][29][30][31][32][33][34][35] , and even less examples display silicon-stereogenic centers. To the best of our knowledge, only Shintani, Hayashi, Nozaki et al and Song have succeeded in forming six-membered tetraorgano-substituted silicon-stereogenic silanes (Fig.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective Construction of Six- and Seven-Membered Triorgano-Substituted Silicon-Stereogenic Heterocycles

Chen

et al. 2020

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A rhodium-catalyzed enantioselective construction of six- and seven-membered triorgano-substituted silicon-stereogenic heterocycles is developed. This process undergoes a direct dehydrogenative C−H silylation, giving access to a wide range of novel triorgano-substituted silicon-stereogenic heterocycles in good to excellent yields and enantioselectivities, that significantly enlarged the chemical space of the silicon-centered chiral molecules. Further elaboration of the chiral monohydrosilane product delivered various corresponding tetraorgano-substituted silicon-stereogenic heterocycles without the loss of enantiopurity. These novel silicon-bridged heterocycles exhibit bright blue fluorescence, which would have potential application prospects in organic optoelectronic materials.

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Construction of Silicon-Containing Seven-Membered Rings by Catalytic [4 + 2 + 1] Cycloaddition through Rhodium Silylenoid

Cited by 21 publications

References 55 publications

Activation of the Si–B interelement bond related to catalysis

Activation of the Si–B interelement bond related to catalysis

Recent Progress in Cyclic Aryliodonium Chemistry: Syntheses and Applications

Enantioselective Construction of Six- and Seven-Membered Triorgano-Substituted Silicon-Stereogenic Heterocycles

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