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UID:b8cb68c7-f893-4cdc-b74c-8f5e6a191459@nexttoyou
DTSTAMP:20261105T160703Z
DTSTART:20261105T193000Z
DTEND:20261105T203000Z
SUMMARY:Mr. Nicholas Wade (University of Illinois Urbana-Champaign) Semina
 r
LOCATION:Chevron Science Center 152\, 219 Parkman Avenue\, Pittsburgh\, PA
  15260
DESCRIPTION:Title: Boronic Ester Design Enables Rapid\, Stereospecific B-A
 lkyl Suzuki-Miyaura Cross-Coupling\n\nAbstract: In the past decades\, the
  Suzuki-Miyaura cross-coupling (SMCC) has been well renowned as the premi
 er method for the facile and selective construction of C(sp2)–C(sp2) bond
 s. In recent years\, B-alkyl SMCC has gained considerable intrigue as a m
 ethod for creation of C(sp2)–C(sp3) linkages for drug discovery and devel
 opment. Despite advances made in both ligand and boronate design\, these 
 challenging cross-coupling reactions typically suffer from poor yields an
 d long reaction times\, stemming from slow transmetalation of alkylborona
 tes and rapid -hydride elimination of alkylpalladium(II) complexes. Previ
 ous work using neopentyl glycol boronic esters and potassium trimethyl si
 lanolate (TMSOK) enabled primary alkyl SMCC to numerous aryl halides. Unf
 ortunately\, these conditions were unsuccessful with secondary alkylboron
 ic esters due to deleterious protodehalogenation arising from the boronic
  ester backbone. Investigation of many sec-butylboronic esters indicated 
 that substitution proximal to the oxygens on the ester skeleton was cruci
 al for circumventing protodehalogenation and enabling productive cross-co
 upling. Thus\, there was a need for a highly reactive boronic ester scaff
 old without the capability to undergo -hydride elimination. Further exper
 imentation led to the identification of a boronate generated in situ from
  tetramethyl-N-methyliminodiacetic acid (TIDA) alkylboronate\n\nhttp://ne
 xt-to-u.app/events/b8cb68c7-f893-4cdc-b74c-8f5e6a191459
URL:http://next-to-u.app/events/b8cb68c7-f893-4cdc-b74c-8f5e6a191459
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