Visible‐Light‐Mediated Charge Transfer Enables C−C Bond Formation with Traceless Acceptor Groups

Michael J. James; Felix Strieth‐kalthoff; Frederik Sandfort; Felix J. R. Klauck; Felicitas Wagener; Frank Glorius

doi:10.1002/chem.201901397

Visible‐Light‐Mediated Charge Transfer Enables C−C Bond Formation with Traceless Acceptor Groups

Michael J. James, Felix Strieth‐kalthoff, Frederik Sandfort, Felix J. R. Klauck, Felicitas Wagener, Frank Glorius

Organic Chemistry Group

University of Munster (Westfalische Wilhelms Universitat Munster)

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

Abstract

The development and application of traceless acceptor groups in photochemical C−C bond formation is described. This strategy was enabled by the photoexcitation of electron donor–acceptor (EDA) complexes with visible light. The traceless acceptors, which were readily prepared from amino acid and peptide feedstocks, could be used to alkylate a wide range of heteroarene and enamine donors under metal- and peroxide-free conditions. The crucial role of the EDA complexes in the mechanism of these reactions was explored through combined experimental and computational studies.

Original language	English
Pages (from-to)	8240-8244
Number of pages	5
Journal	Chemistry – A European Journal
Volume	25
Issue number	35
DOIs	https://doi.org/10.1002/chem.201901397 https://doi.org/10.1002/chem.v25.35
Publication status	Published - 11 Apr 2019

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title = "Visible‐Light‐Mediated Charge Transfer Enables C−C Bond Formation with Traceless Acceptor Groups",

abstract = "The development and application of traceless acceptor groups in photochemical C−C bond formation is described. This strategy was enabled by the photoexcitation of electron donor–acceptor (EDA) complexes with visible light. The traceless acceptors, which were readily prepared from amino acid and peptide feedstocks, could be used to alkylate a wide range of heteroarene and enamine donors under metal- and peroxide-free conditions. The crucial role of the EDA complexes in the mechanism of these reactions was explored through combined experimental and computational studies.",

author = "James, {Michael J.} and Felix Strieth‐kalthoff and Frederik Sandfort and Klauck, {Felix J. R.} and Felicitas Wagener and Frank Glorius",

year = "2019",

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doi = "10.1002/chem.201901397",

language = "English",

volume = "25",

pages = "8240--8244",

journal = "Chemistry – A European Journal",

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T1 - Visible‐Light‐Mediated Charge Transfer Enables C−C Bond Formation with Traceless Acceptor Groups

AU - James, Michael J.

AU - Strieth‐kalthoff, Felix

AU - Sandfort, Frederik

AU - Klauck, Felix J. R.

AU - Wagener, Felicitas

AU - Glorius, Frank

PY - 2019/4/11

Y1 - 2019/4/11

N2 - The development and application of traceless acceptor groups in photochemical C−C bond formation is described. This strategy was enabled by the photoexcitation of electron donor–acceptor (EDA) complexes with visible light. The traceless acceptors, which were readily prepared from amino acid and peptide feedstocks, could be used to alkylate a wide range of heteroarene and enamine donors under metal- and peroxide-free conditions. The crucial role of the EDA complexes in the mechanism of these reactions was explored through combined experimental and computational studies.

AB - The development and application of traceless acceptor groups in photochemical C−C bond formation is described. This strategy was enabled by the photoexcitation of electron donor–acceptor (EDA) complexes with visible light. The traceless acceptors, which were readily prepared from amino acid and peptide feedstocks, could be used to alkylate a wide range of heteroarene and enamine donors under metal- and peroxide-free conditions. The crucial role of the EDA complexes in the mechanism of these reactions was explored through combined experimental and computational studies.

U2 - 10.1002/chem.201901397

DO - 10.1002/chem.201901397

M3 - Article

SN - 0947-6539

VL - 25

SP - 8240

EP - 8244

JO - Chemistry – A European Journal

JF - Chemistry – A European Journal

IS - 35

ER -

Visible‐Light‐Mediated Charge Transfer Enables C−C Bond Formation with Traceless Acceptor Groups

Abstract

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