Rhodium‐Catalyzed Synthesis of Chiral Monohydrosilanes by Intramolecular C−H Functionalization of Dihydrosilanes

The preparation of chiral monohydrosilanes remains a rarely achieved goal. To this end a Rh‐catalyzed desymmetrization of dihydrosilanes by way of intramolecular C(sp2)−H functionalization under simple and mild conditions has now been developed. This method provides easy access to a broad range of c...

Celý popis

Uloženo v:

Podrobná bibliografie
Vydáno v:	Angewandte Chemie International Edition Ročník 60; číslo 8; s. 4245 - 4251
Hlavní autoři:	Ma, Wenpeng, Liu, Li‐Chuan, An, Kun, He, Tao, He, Wei
Médium:	Journal Article
Jazyk:	angličtina
Vydáno:	WEINHEIM Wiley 19.02.2021 Wiley Subscription Services, Inc
Vydání:	International ed. in English
Témata:	Chemical synthesis Chemistry Chemistry, Multidisciplinary desymmetrization dihydrosilanes enantioselectivity monohydrosilane Physical Sciences Rhodium Science & Technology Silicon Silicon compounds Stereochemistry enantioselectivity desymmetrization ASYMMETRIC-SYNTHESIS ENANTIOSELECTIVE SYNTHESIS HYDROSILYLATION dihydrosilanes SILICON-STEREOGENIC SILANES KETONES SILACYCLOBUTANES DEHYDROGENATIVE SILYLATION CONSTRUCTION monohydrosilane BOND ACTIVATION rhodium
ISSN:	1433-7851, 1521-3773, 1521-3773
On-line přístup:	Získat plný text
Tagy:	Přidat tag Žádné tagy, Buďte první, kdo vytvoří štítek k tomuto záznamu!

Popis
Shrnutí:	The preparation of chiral monohydrosilanes remains a rarely achieved goal. To this end a Rh‐catalyzed desymmetrization of dihydrosilanes by way of intramolecular C(sp2)−H functionalization under simple and mild conditions has now been developed. This method provides easy access to a broad range of chiral monohydrosilanes in good yields with excellent enantioselectivities (up to >99 % ee). The resulting monohydrosilanes constitute a good platform to access stereogenic silicon compounds, as well as useful compounds to probe silicon stereochemistry. A Rh‐chiral diphosphine complex was found to catalyze desymmetrization of dihydrosilanes by formal intramolecular Si−H/C−H dehydrogenative coupling reactions. This simple, mild, and practical method results in unprecedently high enantioselectivity and a broad substrate scope. The chiral monohydrosilanes could be further elaborated into various stereogenic silicon compounds in a stereospecific manner.
Bibliografie:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 content type line 23
ISSN:	1433-7851 1521-3773 1521-3773
DOI:	10.1002/anie.202013041