1372205-89-4

Basic information

• Product Name: (Z)-4,4,5,5-tetramethyl-2-(4-(phenylsulfonyl)but-2-en-2-yl)-1,3,2-dioxaborolane
• Synonyms: (Z)-4,4,5,5-tetramethyl-2-(4-(phenylsulfonyl)but-2-en-2-yl)-1,3,2-dioxaborolane
• CAS NO: 1372205-89-4
• Molecular Weight: 322.233
• Mol File: 1372205-89-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (Z)-4,4,5,5-tetramethyl-2-(4-(phenylsulfonyl)but-2-en-2-yl)-1,3,2-dioxaborolane(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-4,4,5,5-tetramethyl-2-(4-(phenylsulfonyl)but-2-en-2-yl)-1,3,2-dioxaborolane(1372205-89-4)
• EPA Substance Registry System: (Z)-4,4,5,5-tetramethyl-2-(4-(phenylsulfonyl)but-2-en-2-yl)-1,3,2-dioxaborolane(1372205-89-4)

Safety Data

• Hazardous Substances Data: 1372205-89-4(Hazardous Substances Data)

Upstream product

• 13603-84-4 1-(phenylsulfonyl)-2-butyne 
• 73183-34-3 bis(pinacol)diborane 

Relevant articles and documents

Regiocontrolled CuI-catalyzed borylation of propargylic- functionalized internal alkynes

Good to excellent reactivity and regiocontrol have been achieved in the CuI-catalyzed borylation of dialkyl internal alkynes with bis(pinacolato)diboron. The presence of a propargylic polar group (OH, OR, SAr, SO2Ar, or NHTs), in combination with PCy3 as ligand, allowed maximizing the reactivity and site-selectivity (β to the propargylic function). DFT calculations suggest a subtle orbitalic influence from the propargylic group, matched with ligand and substrate size effects, as key factors involved in the high β-selectivity. The vinylboronates allowed the stereoselective synthesis of trisubstituted olefins, while allylic substitution of the SO2Py group without affecting the boronate group provided access to formal hydroboration products of unbiased dialkylalkynes.