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4,4,5,5‐Tetraphenyl‐1,3,2‐dioxaborolane: A Bulky Borane for the Transition Metal Catalysed Hydroboration of Alkenes
Author(s) -
Fritschi Claudia B.,
Wernitz Sophie M.,
Vogels Christopher M.,
Shaver Michael P.,
Decken Andreas,
Bell Andrew,
Westcott Stephen A.
Publication year - 2008
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.200701066
Subject(s) - chemistry , hydroboration , borane , rhodium , yield (engineering) , catalysis , transition metal , medicinal chemistry , metal , crystal structure , boranes , organic chemistry , stereochemistry , boron , materials science , metallurgy
4,4,5,5‐Tetraphenyl‐1,3,2‐dioxaborolane (HBBzpin, 3 ) has been prepared in high yield by the addition of H 3 B · SMe 2 to benzopinacol. HBBzpin is a relatively stable solid that reacts with a variety of alkenes under catalytic conditions to give air‐ and chromatography‐stable organoboronate esters. Reactions of vinylarenes in the presence of catalytic amounts of [Cp*IrCl 2 ] 2 gave the corresponding terminal products selectively. Addition of HBBzpin to RhCl(PPh 3 ) 3 gave Rh(H)Cl(BzBpin)(PPh 3 ) 2 ( 11 ) as the only new rhodium‐containing product. The complex 11 has been characterized by a number of physical and analytical methods, including a single‐crystal X‐ray diffraction study. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)