Cyclic (Amino)(Phosphonium Bora‐Ylide)Silanone: A Remarkable Room‐Temperature‐Persistent Silanone. Issue 50 (22nd November 2017)

• Record Type: Journal Article
• Authors: Rosas‐Sánchez, Alfredo; Alvarado‐Beltran, Isabel; Baceiredo, Antoine; Saffon‐Merceron, Nathalie; Massou, Stéphane; Hashizume, Daisuke; Branchadell, Vicenç; Kato, Tsuyoshi
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 50(2017)
• Page Start: 15916
• Page End: 15920
• Publication Date: 2017-11-22
• Subjects: bora-ylides -- borylenes -- N-heterocyclic carbenes -- phosphines -- silanones; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201710358
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: A silanone substituted by bulky amino and phosphonium bora‐ylide substituents has been isolated in crystalline form. Thanks to the exceptionally strong electron‐donating phosphonium bora‐ylide substituent, the lifetime at room temperature of the silanone is dramatically extended ( t 1/2 =4 days) compared to the related (amino)(phosphonium ylide)silanoneVI ( t 1/2 =5 h), allowing easier manipulation and its use as precursor of new valuable silicon compounds. The interaction of silanone with a weak Lewis acid such as MgBr2 increases further its stability (no degradation after 3 weeks at room temperature). Abstract : A silanone substituted with bulky amino and phosphonium bora‐ylide substituents has been synthesized and isolated in crystalline form. Thanks to the exceptionally strong electron‐donating phosphonium‐bora‐ylide substituent, the lifetime is dramatically extended ( t 1/2 =4 days). The interaction with a weak Lewis acid such as MgBr2 increases further its stability, and no degradation of silanone was observed after 3 weeks at room temperature.