σ N-C Bond Difunctionalization in Bridged Twisted Amides: Sew-and-Cut Activation Approach to Functionalized Isoquinolines

Feng Hu; Pradeep Nareddy; Roger Lalancette; Frank Jordan; Michal Szostak

doi:10.1021/acs.orglett.7b00913

σ N-C Bond Difunctionalization in Bridged Twisted Amides: Sew-and-Cut Activation Approach to Functionalized Isoquinolines

Feng Hu, Pradeep Nareddy, Roger Lalancette, Frank Jordan, Michal Szostak

SASN Chemistry

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

16 Scopus citations

Abstract

A rare example of highly selective σ N-C bond difunctionalization in bridged twisted lactams through N-C cleavage has been achieved. In combination with the intramolecular Heck cyclization, this method affords a two-step bond reorganization event (“sew-and-cut”) to access functionalized isoquinoline ring systems directly with high atom economy. C-H bond functionalizations directed by a weakly coordinating bridged amide bond increase scaffold diversity. Preliminary mechanistic studies on the effect of amide distortion and the role of electrophile in this unusual σ N-C amide difunctionalization are described.

Original language	English (US)
Pages (from-to)	2386-2389
Number of pages	4
Journal	Organic letters
Volume	19
Issue number	9
DOIs	https://doi.org/10.1021/acs.orglett.7b00913
State	Published - May 5 2017

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "σ N-C Bond Difunctionalization in Bridged Twisted Amides: Sew-and-Cut Activation Approach to Functionalized Isoquinolines",

abstract = "A rare example of highly selective σ N-C bond difunctionalization in bridged twisted lactams through N-C cleavage has been achieved. In combination with the intramolecular Heck cyclization, this method affords a two-step bond reorganization event (“sew-and-cut”) to access functionalized isoquinoline ring systems directly with high atom economy. C-H bond functionalizations directed by a weakly coordinating bridged amide bond increase scaffold diversity. Preliminary mechanistic studies on the effect of amide distortion and the role of electrophile in this unusual σ N-C amide difunctionalization are described.",

author = "Feng Hu and Pradeep Nareddy and Roger Lalancette and Frank Jordan and Michal Szostak",

note = "Funding Information: Financial support was provided by Rutgers University. The 500 MHz spectrometer was supported by the NSF-MRI grant (CHE-1229030).We thank SEED Grant (Rutgers University) to the Center for Sustainable Synthesis for partial support of this project. Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

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doi = "10.1021/acs.orglett.7b00913",

language = "English (US)",

volume = "19",

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journal = "Organic Letters",

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T1 - σ N-C Bond Difunctionalization in Bridged Twisted Amides

T2 - Sew-and-Cut Activation Approach to Functionalized Isoquinolines

AU - Hu, Feng

AU - Nareddy, Pradeep

AU - Lalancette, Roger

AU - Jordan, Frank

AU - Szostak, Michal

N1 - Funding Information: Financial support was provided by Rutgers University. The 500 MHz spectrometer was supported by the NSF-MRI grant (CHE-1229030).We thank SEED Grant (Rutgers University) to the Center for Sustainable Synthesis for partial support of this project. Publisher Copyright: © 2017 American Chemical Society.

PY - 2017/5/5

Y1 - 2017/5/5

N2 - A rare example of highly selective σ N-C bond difunctionalization in bridged twisted lactams through N-C cleavage has been achieved. In combination with the intramolecular Heck cyclization, this method affords a two-step bond reorganization event (“sew-and-cut”) to access functionalized isoquinoline ring systems directly with high atom economy. C-H bond functionalizations directed by a weakly coordinating bridged amide bond increase scaffold diversity. Preliminary mechanistic studies on the effect of amide distortion and the role of electrophile in this unusual σ N-C amide difunctionalization are described.

AB - A rare example of highly selective σ N-C bond difunctionalization in bridged twisted lactams through N-C cleavage has been achieved. In combination with the intramolecular Heck cyclization, this method affords a two-step bond reorganization event (“sew-and-cut”) to access functionalized isoquinoline ring systems directly with high atom economy. C-H bond functionalizations directed by a weakly coordinating bridged amide bond increase scaffold diversity. Preliminary mechanistic studies on the effect of amide distortion and the role of electrophile in this unusual σ N-C amide difunctionalization are described.

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σ N-C Bond Difunctionalization in Bridged Twisted Amides: Sew-and-Cut Activation Approach to Functionalized Isoquinolines

Abstract

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