1198-34-1Relevant articles and documents
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Bunnett,J.F.,Sundberg,J.E.
, p. 1702 - 1706 (1976)
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Fluorotetraphenylbismuth: A new reagent for efficient regioselective α-phenylation of carbonyl compounds
Ooi, Takashi,Goto, Ryoji,Maruoka, Keiji
, p. 10494 - 10495 (2003)
Synthesis and X-ray crystallographic characterization of fluorotetraphenylbismuth (1) has been achieved for the first time, revealing that the bismuth center of 1 adopts a distorted trigonal bipyramidal geometry with three ipso carbons at the equatorial sites and one ipso carbon and fluorine atom at the apical sites. Contrary to the previous common understanding of this type of organobismuth(V) compound, 1 was found to be thermally stable, maintaining its amphiphilic property. Hence, 1 can be used as an off-the-shelf reagent in organic synthesis, and its utility has been clearly demonstrated in applications to the efficient α-phenylation of ketones and esters. For instance, simple mixing of 1 and 1-trimethylsiloxy-3,4-dihydronaphthalene in THF at -40 °C and stirring at room temperature for 10 min gave rise to 2-phenyl-1-tetralone almost quantitatively without formation of the polyphenylated products. In addition to the generality of this method, applicability of our approach to the selective α-alkenylation of carbonyl compounds was also demonstrated by the use of fluoro(2-phenylethenyl)tris(p-tolyl)bismuth (2) as a representative reagent. These results imply the vast potential of organobismuth(V) compounds of type 1 and 2 as useful precursors of a wide variety of pentavalent organobismuth compounds based on the utilization of the eminent fluorine-silicon interaction or the inherent basicity of the fluorine atom. Copyright
Catalytic diazoalkane-carbonyl homologation: Synthesis of 2,2-diphenylcycloheptanone and other quaternary or tertiary arylalkanones and spirocycles by ring expansion
Burman, Jacob S.,Kingsbury, Jason S.,Rendina, Victor L.,Smolarski, Brittany A.
, p. 343 - 365 (2021/11/08)
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Identification and Preclinical Evaluation of the Bicyclic Pyrimidine γ-Secretase Modulator BMS-932481
Boy, Kenneth M.,Guernon, Jason M.,Zuev, Dmitry S.,Xu, Li,Zhang, Yunhui,Shi, Jianliang,Marcin, Lawrence R.,Higgins, Mendi A.,Wu, Yong-Jin,Krishnananthan, Subramaniam,Li, Jianqing,Trehan, Ashok,Smith, Daniel,Toyn, Jeremy H.,Meredith, Jere E.,Burton, Catherine R.,Kimura, S. Roy,Zvyaga, Tatyana,Zhuo, Xiaoliang,Lentz, Kimberley A.,Grace, James E.,Denton, Rex,Morrison, John S.,Mathur, Arvind,Albright, Charles F.,Ahlijanian, Michael K.,Olson, Richard E.,Thompson, Lorin A.,Macor, John E.
supporting information, p. 312 - 317 (2019/03/08)
A triazine hit identified from a screen of the BMS compound collection was optimized for potency, in vivo activity, and off-target profile to produce the bicyclic pyrimidine γ-secretase modulator BMS-932481. The compound showed robust reductions of Aβsub
