Oxidative ring closure and metal triggered ring opening: Syntheses of macrocyclic and linear hexapyrroles

Kai Zhang; Pingchun Wei; Xin Li; Hans Ågren; Yongshu Xie

doi:10.1021/ol503132r

Oxidative ring closure and metal triggered ring opening: Syntheses of macrocyclic and linear hexapyrroles

Kai Zhang
, Pingchun Wei
, Xin Li
, Hans Ågren
, Yongshu Xie^*

^*Corresponding author for this work

East China University of Science and Technology
KTH Royal Institute of Technology

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

19 Scopus citations

Abstract

A C₆F₅-substituted hexapyrrane (1) was synthesized in one step. Oxidative cyclization of 1 with DDQ afforded a phlorin-dipyrrin conjugate (2), and subsequent FeCl₃-assisted oxidative cleavage of 2 afforded a terminally di-α-methoxy substituted hexapyrrin (3). On the other hand, oxidation of 1 with FeCl₃ afforded 3, a hexapyrrinone Fe³⁺ complex (4), and a hexaphyrin (1,1,1,1,1,0) (5). These results indicate that the oxidation of hexapyrranes may be developed as an effective approach for the syntheses of novel linear and macrocyclic hexapyrroles.

Original language	English
Pages (from-to)	6354-6357
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	24
DOIs	https://doi.org/10.1021/ol503132r
State	Published - 19 Dec 2014
Externally published	Yes

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@article{81a3b573ad9b45c8afd51212c32c4439,

title = "Oxidative ring closure and metal triggered ring opening: Syntheses of macrocyclic and linear hexapyrroles",

abstract = "A C6F5-substituted hexapyrrane (1) was synthesized in one step. Oxidative cyclization of 1 with DDQ afforded a phlorin-dipyrrin conjugate (2), and subsequent FeCl3-assisted oxidative cleavage of 2 afforded a terminally di-α-methoxy substituted hexapyrrin (3). On the other hand, oxidation of 1 with FeCl3 afforded 3, a hexapyrrinone Fe3+ complex (4), and a hexaphyrin (1,1,1,1,1,0) (5). These results indicate that the oxidation of hexapyrranes may be developed as an effective approach for the syntheses of novel linear and macrocyclic hexapyrroles.",

author = "Kai Zhang and Pingchun Wei and Xin Li and Hans {\AA}gren and Yongshu Xie",

note = "Publisher Copyright: {\textcopyright} 2014 American Chemical Society.",

year = "2014",

month = dec,

day = "19",

doi = "10.1021/ol503132r",

language = "英语",

volume = "16",

pages = "6354--6357",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "24",

}

TY - JOUR

T1 - Oxidative ring closure and metal triggered ring opening

T2 - Syntheses of macrocyclic and linear hexapyrroles

AU - Zhang, Kai

AU - Wei, Pingchun

AU - Li, Xin

AU - Ågren, Hans

AU - Xie, Yongshu

PY - 2014/12/19

Y1 - 2014/12/19

N2 - A C6F5-substituted hexapyrrane (1) was synthesized in one step. Oxidative cyclization of 1 with DDQ afforded a phlorin-dipyrrin conjugate (2), and subsequent FeCl3-assisted oxidative cleavage of 2 afforded a terminally di-α-methoxy substituted hexapyrrin (3). On the other hand, oxidation of 1 with FeCl3 afforded 3, a hexapyrrinone Fe3+ complex (4), and a hexaphyrin (1,1,1,1,1,0) (5). These results indicate that the oxidation of hexapyrranes may be developed as an effective approach for the syntheses of novel linear and macrocyclic hexapyrroles.

AB - A C6F5-substituted hexapyrrane (1) was synthesized in one step. Oxidative cyclization of 1 with DDQ afforded a phlorin-dipyrrin conjugate (2), and subsequent FeCl3-assisted oxidative cleavage of 2 afforded a terminally di-α-methoxy substituted hexapyrrin (3). On the other hand, oxidation of 1 with FeCl3 afforded 3, a hexapyrrinone Fe3+ complex (4), and a hexaphyrin (1,1,1,1,1,0) (5). These results indicate that the oxidation of hexapyrranes may be developed as an effective approach for the syntheses of novel linear and macrocyclic hexapyrroles.

UR - https://www.scopus.com/pages/publications/84919685142

U2 - 10.1021/ol503132r

DO - 10.1021/ol503132r

M3 - 文章

AN - SCOPUS:84919685142

SN - 1523-7060

VL - 16

SP - 6354

EP - 6357

JO - Organic Letters

JF - Organic Letters

IS - 24

ER -

Oxidative ring closure and metal triggered ring opening: Syntheses of macrocyclic and linear hexapyrroles

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