1,3-γ-Silyl-elimination in electron-deficient cationic systems

Michael A. Mercadante; Christopher B. Kelly; Trevor A. Hamlin; Kayla R. Delle Chiaie; Michael D. Drago; Katherine K. Duffy; Megan T. Dumas; Diana C. Fager; Bryanna L. C. Glod; Katherine E. Hansen; Cameron R. Hill; Rebecca M. Leising; Catherine L. Lynes; Allyson E. MacInnis; Madeline R. McGohey; Stephanie A. Murray; Marc C. Piquette; Shaina L. Roy; Ryan M. Smith; Katherine R. Sullivan; Bao H. Truong; Kristina M. Vailonis; Vitaliy Gorbatyuk; Nicholas E. Leadbeater; Nicholas E. Leadbeater; Leon J. Tilley

doi:10.1039/C4SC01732C

1,3-γ-Silyl-elimination in electron-deficient cationic systems

Michael A. Mercadante
, Christopher B. Kelly
, Trevor A. Hamlin
, Kayla R. Delle Chiaie
, Michael D. Drago
, Katherine K. Duffy
, Megan T. Dumas
, Diana C. Fager
, Bryanna L. C. Glod
, Katherine E. Hansen
, Cameron R. Hill
, Rebecca M. Leising
, Catherine L. Lynes
, Allyson E. MacInnis
, Madeline R. McGohey
, Stephanie A. Murray
, Marc C. Piquette
, Shaina L. Roy
, Ryan M. Smith
, Katherine R. Sullivan

Bao H. Truong, Kristina M. Vailonis, Vitaliy Gorbatyuk, Nicholas E. Leadbeater, Nicholas E. Leadbeater, Leon J. Tilley

Research output: Contribution to journal › Article › peer-review

Original language	American English
Journal	Chemical Science
Volume	5
DOIs	https://doi.org/10.1039/C4SC01732C
State	Published - Jul 3 2014

Disciplines

Organic Chemistry
Chemistry

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Mercadante, M. A., Kelly, C. B., Hamlin, T. A., Chiaie, K. R. D., Drago, M. D., Duffy, K. K., Dumas, M. T., Fager, D. C., Glod, B. L. C., Hansen, K. E., Hill, C. R., Leising, R. M., Lynes, C. L., MacInnis, A. E., McGohey, M. R., Murray, S. A., Piquette, M. C., Roy, S. L., Smith, R. M., ... Tilley, L. J. (2014). 1,3-γ-Silyl-elimination in electron-deficient cationic systems. Chemical Science, 5. https://doi.org/10.1039/C4SC01732C

Mercadante, MA, Kelly, CB, Hamlin, TA, Chiaie, KRD, Drago, MD, Duffy, KK, Dumas, MT, Fager, DC, Glod, BLC, Hansen, KE, Hill, CR, Leising, RM, Lynes, CL, MacInnis, AE, McGohey, MR, Murray, SA, Piquette, MC, Roy, SL, Smith, RM, Sullivan, KR, Truong, BH, Vailonis, KM, Gorbatyuk, V, Leadbeater, NE, Leadbeater, NE & Tilley, LJ 2014, '1,3-γ-Silyl-elimination in electron-deficient cationic systems', Chemical Science, vol. 5. https://doi.org/10.1039/C4SC01732C

@article{d4f4d7bb0fbc45f5bacdfce78a7a566d,

title = "1,3-γ-Silyl-elimination in electron-deficient cationic systems",

author = "Mercadante, \{Michael A.\} and Kelly, \{Christopher B.\} and Hamlin, \{Trevor A.\} and Chiaie, \{Kayla R. Delle\} and Drago, \{Michael D.\} and Duffy, \{Katherine K.\} and Dumas, \{Megan T.\} and Fager, \{Diana C.\} and Glod, \{Bryanna L. C.\} and Hansen, \{Katherine E.\} and Hill, \{Cameron R.\} and Leising, \{Rebecca M.\} and Lynes, \{Catherine L.\} and MacInnis, \{Allyson E.\} and McGohey, \{Madeline R.\} and Murray, \{Stephanie A.\} and Piquette, \{Marc C.\} and Roy, \{Shaina L.\} and Smith, \{Ryan M.\} and Sullivan, \{Katherine R.\} and Truong, \{Bao H.\} and Vailonis, \{Kristina M.\} and Vitaliy Gorbatyuk and Leadbeater, \{Nicholas E.\} and Leadbeater, \{Nicholas E.\} and Tilley, \{Leon J.\}",

note = "Placement of an electron-withdrawing trifluoromethyl group (-CF) at a putative cationic centre enhances γ-silyl neighbouring-group participation (NGP). In stark contrast to previously studied γ-silyl-substituted systems, the preferred reaction pathway is 1,3-γ-silyl elimination, giving ring closure over solvent substitution or alkene formation.",

year = "2014",

month = jul,

day = "3",

doi = "10.1039/C4SC01732C",

language = "American English",

volume = "5",

journal = "Chemical Science",

}

TY - JOUR

T1 - 1,3-γ-Silyl-elimination in electron-deficient cationic systems

AU - Mercadante, Michael A.

AU - Kelly, Christopher B.

AU - Hamlin, Trevor A.

AU - Chiaie, Kayla R. Delle

AU - Drago, Michael D.

AU - Duffy, Katherine K.

AU - Dumas, Megan T.

AU - Fager, Diana C.

AU - Glod, Bryanna L. C.

AU - Hansen, Katherine E.

AU - Hill, Cameron R.

AU - Leising, Rebecca M.

AU - Lynes, Catherine L.

AU - MacInnis, Allyson E.

AU - McGohey, Madeline R.

AU - Murray, Stephanie A.

AU - Piquette, Marc C.

AU - Roy, Shaina L.

AU - Smith, Ryan M.

AU - Sullivan, Katherine R.

AU - Truong, Bao H.

AU - Vailonis, Kristina M.

AU - Gorbatyuk, Vitaliy

AU - Leadbeater, Nicholas E.

AU - Tilley, Leon J.

N1 - Placement of an electron-withdrawing trifluoromethyl group (-CF) at a putative cationic centre enhances γ-silyl neighbouring-group participation (NGP). In stark contrast to previously studied γ-silyl-substituted systems, the preferred reaction pathway is 1,3-γ-silyl elimination, giving ring closure over solvent substitution or alkene formation.

PY - 2014/7/3

Y1 - 2014/7/3

UR - http://xlink.rsc.org/?DOI=C4SC01732C

U2 - 10.1039/C4SC01732C

DO - 10.1039/C4SC01732C

M3 - Article

VL - 5

JO - Chemical Science

JF - Chemical Science

ER -

1,3-γ-Silyl-elimination in electron-deficient cationic systems

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