Azido-Enolonium Species in C-C and C-N Bond-Forming Coupling Reactions

Atul A. More; Sourav K. Santra; Alex M. Szpilman

doi:10.1021/acs.orglett.9b03824

Azido-Enolonium Species in C-C and C-N Bond-Forming Coupling Reactions

Atul A. More
, Sourav K. Santra
, Alex M. Szpilman

מדעי הכימיה

פרסום מחקרי: פרסום בכתב עת › מאמר › ביקורת עמיתים

22 ציטוטים ‏(Scopus)

תקציר

Vinyl azides react with boron trifluoride activated Koser's hypervalent iodine reagent to afford azido-enolonium species. These previously unknown azido-enolonium species react efficiently with aromatic compounds, allyltrimethylsilane, and azoles under mild conditions, with no need for a transition-metal catalyst, forming C-C and C-N bonds to give a variety of α-functionalized ketones. The intermediacy of the proposed azido-enolonium species is supported by spectroscopic studies.

שפה מקורית	אנגלית
עמודים (מ-עד)	768-771
מספר עמודים	4
כתב עת	Organic Letters
כרך	22
מספר גיליון	3
מזהי עצם דיגיטלי (DOIs)	https://doi.org/10.1021/acs.orglett.9b03824
סטטוס פרסום	פורסם - 7 פבר׳ 2020

גישה למסמך

10.1021/acs.orglett.9b03824

קבצים וקישורים אחרים

Link to publication in Scopus

פורמט ציטוט ביבליוגרפי

@article{f5a7436799364172a3473074759f4f5e,

title = "Azido-Enolonium Species in C-C and C-N Bond-Forming Coupling Reactions",

abstract = "Vinyl azides react with boron trifluoride activated Koser's hypervalent iodine reagent to afford azido-enolonium species. These previously unknown azido-enolonium species react efficiently with aromatic compounds, allyltrimethylsilane, and azoles under mild conditions, with no need for a transition-metal catalyst, forming C-C and C-N bonds to give a variety of α-functionalized ketones. The intermediacy of the proposed azido-enolonium species is supported by spectroscopic studies.",

author = "More, \{Atul A.\} and Santra, \{Sourav K.\} and Szpilman, \{Alex M.\}",

note = "Publisher Copyright: {\textcopyright} 2020 American Chemical Society.",

year = "2020",

month = feb,

day = "7",

doi = "10.1021/acs.orglett.9b03824",

language = "אנגלית",

volume = "22",

pages = "768--771",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "3",

}

TY - JOUR

T1 - Azido-Enolonium Species in C-C and C-N Bond-Forming Coupling Reactions

AU - More, Atul A.

AU - Santra, Sourav K.

AU - Szpilman, Alex M.

PY - 2020/2/7

Y1 - 2020/2/7

N2 - Vinyl azides react with boron trifluoride activated Koser's hypervalent iodine reagent to afford azido-enolonium species. These previously unknown azido-enolonium species react efficiently with aromatic compounds, allyltrimethylsilane, and azoles under mild conditions, with no need for a transition-metal catalyst, forming C-C and C-N bonds to give a variety of α-functionalized ketones. The intermediacy of the proposed azido-enolonium species is supported by spectroscopic studies.

AB - Vinyl azides react with boron trifluoride activated Koser's hypervalent iodine reagent to afford azido-enolonium species. These previously unknown azido-enolonium species react efficiently with aromatic compounds, allyltrimethylsilane, and azoles under mild conditions, with no need for a transition-metal catalyst, forming C-C and C-N bonds to give a variety of α-functionalized ketones. The intermediacy of the proposed azido-enolonium species is supported by spectroscopic studies.

UR - https://www.scopus.com/pages/publications/85078336198

U2 - 10.1021/acs.orglett.9b03824

DO - 10.1021/acs.orglett.9b03824

M3 - ???researchoutput.researchoutputtypes.contributiontojournal.article???

C2 - 31916772

AN - SCOPUS:85078336198

SN - 1523-7060

VL - 22

SP - 768

EP - 771

JO - Organic Letters

JF - Organic Letters

IS - 3

ER -

Azido-Enolonium Species in C-C and C-N Bond-Forming Coupling Reactions

תקציר

גישה למסמך

קבצים וקישורים אחרים

טביעת אצבע

פורמט ציטוט ביבליוגרפי