Oxidations of pyrrolidines and piperidines to afford CH-functionalized isopropyl-1-carboxylate congeners

Steven Gunawan; Nathan Bedard; Christopher Foley; Christopher Hulme

doi:10.1016/j.tetlet.2021.152978

Oxidations of pyrrolidines and piperidines to afford CH-functionalized isopropyl-1-carboxylate congeners

Steven Gunawan, Nathan Bedard, Christopher Foley, Christopher Hulme

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

Abstract

This article describes the action of iodine(III) reagents [diacetoxyiodobenzene, PhI(OAc)₂, and iodosobenzene, (PhIO)_n] in conjunction with TMSBr which act as functional bromine equivalents in unique oxidations of saturated, carbamate protected N-heterocycles. Interestingly, during this work, treatment of the same carbamates with molecular bromine alone afforded similar products, which were sequestered by the solvent methanol.

Original language	English (US)
Article number	152978
Journal	Tetrahedron Letters
Volume	69
DOIs	https://doi.org/10.1016/j.tetlet.2021.152978
State	Published - Apr 13 2021

Keywords

Bromination
CH-functionalization
Hypervalent iodine
N-acyliminium
N-bromosuccinimide
Radical

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2021.152978

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title = "Oxidations of pyrrolidines and piperidines to afford CH-functionalized isopropyl-1-carboxylate congeners",

abstract = "This article describes the action of iodine(III) reagents [diacetoxyiodobenzene, PhI(OAc)2, and iodosobenzene, (PhIO)n] in conjunction with TMSBr which act as functional bromine equivalents in unique oxidations of saturated, carbamate protected N-heterocycles. Interestingly, during this work, treatment of the same carbamates with molecular bromine alone afforded similar products, which were sequestered by the solvent methanol.",

keywords = "Bromination, CH-functionalization, Hypervalent iodine, N-acyliminium, N-bromosuccinimide, Radical",

author = "Steven Gunawan and Nathan Bedard and Christopher Foley and Christopher Hulme",

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year = "2021",

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doi = "10.1016/j.tetlet.2021.152978",

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T1 - Oxidations of pyrrolidines and piperidines to afford CH-functionalized isopropyl-1-carboxylate congeners

AU - Gunawan, Steven

AU - Bedard, Nathan

AU - Foley, Christopher

AU - Hulme, Christopher

PY - 2021/4/13

Y1 - 2021/4/13

N2 - This article describes the action of iodine(III) reagents [diacetoxyiodobenzene, PhI(OAc)2, and iodosobenzene, (PhIO)n] in conjunction with TMSBr which act as functional bromine equivalents in unique oxidations of saturated, carbamate protected N-heterocycles. Interestingly, during this work, treatment of the same carbamates with molecular bromine alone afforded similar products, which were sequestered by the solvent methanol.

AB - This article describes the action of iodine(III) reagents [diacetoxyiodobenzene, PhI(OAc)2, and iodosobenzene, (PhIO)n] in conjunction with TMSBr which act as functional bromine equivalents in unique oxidations of saturated, carbamate protected N-heterocycles. Interestingly, during this work, treatment of the same carbamates with molecular bromine alone afforded similar products, which were sequestered by the solvent methanol.

KW - Bromination

KW - CH-functionalization

KW - Hypervalent iodine

KW - N-acyliminium

KW - N-bromosuccinimide

KW - Radical

UR - https://www.scopus.com/pages/publications/85103300037

UR - https://www.scopus.com/inward/citedby.url?scp=85103300037&partnerID=8YFLogxK

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DO - 10.1016/j.tetlet.2021.152978

M3 - Article

AN - SCOPUS:85103300037

SN - 0040-4039

VL - 69

JO - Tetrahedron Letters

JF - Tetrahedron Letters

M1 - 152978

ER -

Oxidations of pyrrolidines and piperidines to afford CH-functionalized isopropyl-1-carboxylate congeners

Abstract

Keywords

ASJC Scopus subject areas

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