Me3Si−SiMe2[oCON(iPr)2−C6H4]: An Unsymmetrical Disilane Reagent for Regio‐ and Stereoselective Bis‐Silylation of Alkynes. Issue 17 (12th March 2018)

• Record Type: Journal Article
• Authors: Xiao, Peihong; Cao, Yanjun; Gui, Yingying; Gao, Lu; Song, Zhenlei
• Is Part Of: Angewandte Chemie international edition. Volume 57:Issue 17(2018)
• Page Start: 4769
• Page End: 4773
• Publication Date: 2018-03-12
• Subjects: alkynes -- amide -- bis-silylation -- disilanes -- vinylsilanes; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201800513
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: The air‐stable unsymmetrical disilane Me3 Si−SiMe2 [ o CON( i Pr)2 C6 H4 ] has been developed for bis‐silylation of alkynes. This reagent tolerates a range of functional groups, providing Z ‐vinyl disilanes in high yields. It is proposed that the phenyl‐ring‐tethered amide group directs oxidative addition of Pd 0 into the Si−Si bond, which might facilitate formation of a six‐membered Pd cycle, generating products with good to excellent regioselectivity. Abstract : Open Si‐Si‐Me : Air‐stable asymmetric disilane, Me3 Si−SiMe2 [ o CON( i Pr)2 C6 H4 ], was developed for bis‐silylation of alkynes. A range of functional groups are tolerated, providing Z ‐vinyl disilanes in high yields. A phenyl‐ring‐tethered amide group is proposed that directs oxidative addition of Pd 0 into the Si−Si bond, forming a six‐membered Pd cycle and generating products with good to excellent regioselectivity. Key: regioselectivity ratio (r.r.).