Synthesis of Bridged Bicyclic Amines by Intramolecular Amination of Remote C-H Bonds: Synergistic Activation by Light and Heat

Michaelyn C. Lux; Justin Jurczyk; Yu Hong Lam; Zhiguo J. Song; Chao Ma; Jose B. Roque; Jin Su Ham; Nunzio Sciammetta; Donovon Adpressa; Richmond Sarpong; Charles S. Yeung

doi:10.1021/acs.orglett.0c02345

Synthesis of Bridged Bicyclic Amines by Intramolecular Amination of Remote C-H Bonds: Synergistic Activation by Light and Heat

Michaelyn C. Lux, Justin Jurczyk, Yu Hong Lam, Zhiguo J. Song, Chao Ma, Jose B. Roque, Jin Su Ham, Nunzio Sciammetta, Donovon Adpressa, Richmond Sarpong, Charles S. Yeung

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

10 Scopus citations

Abstract

The construction of complex aza-cycles is of interest to drug discovery due to the prevalence of nitrogen-containing heterocycles in pharmaceutical agents. Herein we report an intramolecular C-H amination approach to afford value-added and complexity-enriched bridged bicyclic amines. Guided by density functional theory and nuclear magnetic resonance investigations, we determined the unique roles of light and heat activation in the bicyclization mechanism. We applied both light and heat activation in a synergistic fashion, achieving gram-scale bridged aza-cycle synthesis.

Original language	English (US)
Pages (from-to)	6578-6583
Number of pages	6
Journal	Organic letters
Volume	22
Issue number	16
DOIs	https://doi.org/10.1021/acs.orglett.0c02345
State	Published - Aug 21 2020
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.0c02345

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title = "Synthesis of Bridged Bicyclic Amines by Intramolecular Amination of Remote C-H Bonds: Synergistic Activation by Light and Heat",

abstract = "The construction of complex aza-cycles is of interest to drug discovery due to the prevalence of nitrogen-containing heterocycles in pharmaceutical agents. Herein we report an intramolecular C-H amination approach to afford value-added and complexity-enriched bridged bicyclic amines. Guided by density functional theory and nuclear magnetic resonance investigations, we determined the unique roles of light and heat activation in the bicyclization mechanism. We applied both light and heat activation in a synergistic fashion, achieving gram-scale bridged aza-cycle synthesis.",

author = "Lux, {Michaelyn C.} and Justin Jurczyk and Lam, {Yu Hong} and Song, {Zhiguo J.} and Chao Ma and Roque, {Jose B.} and Ham, {Jin Su} and Nunzio Sciammetta and Donovon Adpressa and Richmond Sarpong and Yeung, {Charles S.}",

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

year = "2020",

month = aug,

day = "21",

doi = "10.1021/acs.orglett.0c02345",

language = "English (US)",

volume = "22",

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journal = "Organic letters",

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TY - JOUR

T1 - Synthesis of Bridged Bicyclic Amines by Intramolecular Amination of Remote C-H Bonds

T2 - Synergistic Activation by Light and Heat

AU - Lux, Michaelyn C.

AU - Jurczyk, Justin

AU - Lam, Yu Hong

AU - Song, Zhiguo J.

AU - Ma, Chao

AU - Roque, Jose B.

AU - Ham, Jin Su

AU - Sciammetta, Nunzio

AU - Adpressa, Donovon

AU - Sarpong, Richmond

AU - Yeung, Charles S.

PY - 2020/8/21

Y1 - 2020/8/21

N2 - The construction of complex aza-cycles is of interest to drug discovery due to the prevalence of nitrogen-containing heterocycles in pharmaceutical agents. Herein we report an intramolecular C-H amination approach to afford value-added and complexity-enriched bridged bicyclic amines. Guided by density functional theory and nuclear magnetic resonance investigations, we determined the unique roles of light and heat activation in the bicyclization mechanism. We applied both light and heat activation in a synergistic fashion, achieving gram-scale bridged aza-cycle synthesis.

AB - The construction of complex aza-cycles is of interest to drug discovery due to the prevalence of nitrogen-containing heterocycles in pharmaceutical agents. Herein we report an intramolecular C-H amination approach to afford value-added and complexity-enriched bridged bicyclic amines. Guided by density functional theory and nuclear magnetic resonance investigations, we determined the unique roles of light and heat activation in the bicyclization mechanism. We applied both light and heat activation in a synergistic fashion, achieving gram-scale bridged aza-cycle synthesis.

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SN - 1523-7060

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JO - Organic letters

JF - Organic letters

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Synthesis of Bridged Bicyclic Amines by Intramolecular Amination of Remote C-H Bonds: Synergistic Activation by Light and Heat

Abstract

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