Abstract
Pd(ITMe)2(PhC≡CPh) acts as a highly reactive precatalyst in the silaboration of terminal and internal alkynes to yield a number of known and novel 1-silyl-2-boryl alkenes. Unprecedented mild reaction temperatures for terminal alkynes, short reaction times, and low catalytic loadings are reported. During mechanistic studies, cis-Pd(ITMe)2(SiMe2Ph)(Bpin) was directly synthesized by oxidative addition of PhMe2SiBpin to Pd(ITMe)2(PhC≡CPh). This represents a very rare example of a (silyl)(boryl)palladium complex. A plausible catalyst decomposition route was also examined.
Highlights
Pd(ITMe)2(PhC CPh) acts as a highly reactive precatalyst in the silaboration of terminal and internal alkynes to yield a number of known and novel 1-silyl-2-boryl alkenes
The most effective alkyne silaboration protocol is the palladium diacetate/isocyanide combination reported by Ito and coworkers (Scheme 1).[13,14]
The reactions proceed with high stereoselectivity toward the syn-1,2-addition products and in the case of terminal alkynes high regioselectivity, with the boryl fragment attached to the terminal position
Summary
Pd(ITMe)2(PhC CPh) acts as a highly reactive precatalyst in the silaboration of terminal and internal alkynes to yield a number of known and novel 1-silyl-2-boryl alkenes. We report the use of Pd(ITMe)2(PhC CPh) in the silaboration of sterically and electronically demanding terminal and symmetrical internal alkynes.
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