CITU: A Peptide and Decarboxylative Coupling Reagent

Justine N. Degruyter, Lara R. Malins, Laurin Wimmer, Khalyd J. Clay, Javier Lopez-Ogalla, Tian Qin, Josep Cornella, Zhiqing Liu, Guanda Che, Denghui Bao, Jason M. Stevens, Jennifer X. Qiao, Martin P. Allen, Michael A. Poss, Phil S. Baran

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Tetrachloro-N-hydroxyphthalimide tetramethyluronium hexafluorophosphate (CITU) is disclosed as a convenient and economical reagent for both acylation and decarboxylative cross-coupling chemistries. Within the former set of reactions, CITU displays reactivity similar to that of common coupling reagents, but with increased safety and reduced cost. Within the latter, increased yields, more rapid conversion, and a simplified procedure are possible across a range of reported decarboxylative transformations.

Original languageEnglish (US)
Pages (from-to)6196-6199
Number of pages4
JournalOrganic Letters
Volume19
Issue number22
DOIs
StatePublished - Nov 17 2017
Externally publishedYes

Fingerprint

peptides
reagents
acylation
Acylation
Peptides
cross coupling
safety
reactivity
Display devices
chemistry
costs
Safety
Costs and Cost Analysis
Costs
N-hydroxyphthalimide

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Degruyter, J. N., Malins, L. R., Wimmer, L., Clay, K. J., Lopez-Ogalla, J., Qin, T., ... Baran, P. S. (2017). CITU: A Peptide and Decarboxylative Coupling Reagent. Organic Letters, 19(22), 6196-6199. https://doi.org/10.1021/acs.orglett.7b03121

CITU : A Peptide and Decarboxylative Coupling Reagent. / Degruyter, Justine N.; Malins, Lara R.; Wimmer, Laurin; Clay, Khalyd J.; Lopez-Ogalla, Javier; Qin, Tian; Cornella, Josep; Liu, Zhiqing; Che, Guanda; Bao, Denghui; Stevens, Jason M.; Qiao, Jennifer X.; Allen, Martin P.; Poss, Michael A.; Baran, Phil S.

In: Organic Letters, Vol. 19, No. 22, 17.11.2017, p. 6196-6199.

Research output: Contribution to journalArticle

Degruyter, JN, Malins, LR, Wimmer, L, Clay, KJ, Lopez-Ogalla, J, Qin, T, Cornella, J, Liu, Z, Che, G, Bao, D, Stevens, JM, Qiao, JX, Allen, MP, Poss, MA & Baran, PS 2017, 'CITU: A Peptide and Decarboxylative Coupling Reagent', Organic Letters, vol. 19, no. 22, pp. 6196-6199. https://doi.org/10.1021/acs.orglett.7b03121
Degruyter JN, Malins LR, Wimmer L, Clay KJ, Lopez-Ogalla J, Qin T et al. CITU: A Peptide and Decarboxylative Coupling Reagent. Organic Letters. 2017 Nov 17;19(22):6196-6199. https://doi.org/10.1021/acs.orglett.7b03121
Degruyter, Justine N. ; Malins, Lara R. ; Wimmer, Laurin ; Clay, Khalyd J. ; Lopez-Ogalla, Javier ; Qin, Tian ; Cornella, Josep ; Liu, Zhiqing ; Che, Guanda ; Bao, Denghui ; Stevens, Jason M. ; Qiao, Jennifer X. ; Allen, Martin P. ; Poss, Michael A. ; Baran, Phil S. / CITU : A Peptide and Decarboxylative Coupling Reagent. In: Organic Letters. 2017 ; Vol. 19, No. 22. pp. 6196-6199.
@article{986a92c565904b5095e97b58d452ed93,
title = "CITU: A Peptide and Decarboxylative Coupling Reagent",
abstract = "Tetrachloro-N-hydroxyphthalimide tetramethyluronium hexafluorophosphate (CITU) is disclosed as a convenient and economical reagent for both acylation and decarboxylative cross-coupling chemistries. Within the former set of reactions, CITU displays reactivity similar to that of common coupling reagents, but with increased safety and reduced cost. Within the latter, increased yields, more rapid conversion, and a simplified procedure are possible across a range of reported decarboxylative transformations.",
author = "Degruyter, {Justine N.} and Malins, {Lara R.} and Laurin Wimmer and Clay, {Khalyd J.} and Javier Lopez-Ogalla and Tian Qin and Josep Cornella and Zhiqing Liu and Guanda Che and Denghui Bao and Stevens, {Jason M.} and Qiao, {Jennifer X.} and Allen, {Martin P.} and Poss, {Michael A.} and Baran, {Phil S.}",
year = "2017",
month = "11",
day = "17",
doi = "10.1021/acs.orglett.7b03121",
language = "English (US)",
volume = "19",
pages = "6196--6199",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "22",

}

TY - JOUR

T1 - CITU

T2 - A Peptide and Decarboxylative Coupling Reagent

AU - Degruyter, Justine N.

AU - Malins, Lara R.

AU - Wimmer, Laurin

AU - Clay, Khalyd J.

AU - Lopez-Ogalla, Javier

AU - Qin, Tian

AU - Cornella, Josep

AU - Liu, Zhiqing

AU - Che, Guanda

AU - Bao, Denghui

AU - Stevens, Jason M.

AU - Qiao, Jennifer X.

AU - Allen, Martin P.

AU - Poss, Michael A.

AU - Baran, Phil S.

PY - 2017/11/17

Y1 - 2017/11/17

N2 - Tetrachloro-N-hydroxyphthalimide tetramethyluronium hexafluorophosphate (CITU) is disclosed as a convenient and economical reagent for both acylation and decarboxylative cross-coupling chemistries. Within the former set of reactions, CITU displays reactivity similar to that of common coupling reagents, but with increased safety and reduced cost. Within the latter, increased yields, more rapid conversion, and a simplified procedure are possible across a range of reported decarboxylative transformations.

AB - Tetrachloro-N-hydroxyphthalimide tetramethyluronium hexafluorophosphate (CITU) is disclosed as a convenient and economical reagent for both acylation and decarboxylative cross-coupling chemistries. Within the former set of reactions, CITU displays reactivity similar to that of common coupling reagents, but with increased safety and reduced cost. Within the latter, increased yields, more rapid conversion, and a simplified procedure are possible across a range of reported decarboxylative transformations.

UR - http://www.scopus.com/inward/record.url?scp=85034609583&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85034609583&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.7b03121

DO - 10.1021/acs.orglett.7b03121

M3 - Article

C2 - 29115835

AN - SCOPUS:85034609583

VL - 19

SP - 6196

EP - 6199

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 22

ER -