Synthesis of meso-5-azaindolyl-appended Zn(II) porphyrins via Pd-catalyzed annulation

Chihiro Maeda; Hiroshi Shinokubo; Atsuhiro Osuka

doi:10.1021/ol070885k

Synthesis of meso-5-azaindolyl-appended Zn(II) porphyrins via Pd-catalyzed annulation

Chihiro Maeda, Hiroshi Shinokubo, Atsuhiro Osuka

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

20 Citations (Scopus)

Abstract

Pd-catalyzed annulation reaction of meso-hexynyl Zn(II) porphyrin with 4-amlno-3-lodopyrldlne efficiently provides meso-3-{5-azaindolyl)-substituted Zn(II) porphyrin as a major product, which assembles to form a slipped cofacial dimer by the complementary coordination of the pyridine molety to the Zn(II) center. 2-Iodoaniline and 2-Iodophenol also undergo this [3 + 2] annulation with the meso-hexynyl Zn(II) porphyrin to furnish meso-Indolyl- and benzofuranyl-substituted Zn(II) porphyrins, respectively.

Original language	English
Pages (from-to)	2493-2496
Number of pages	4
Journal	Organic Letters
Volume	9
Issue number	13
DOIs	https://doi.org/10.1021/ol070885k
Publication status	Published - Jun 21 2007
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/ol070885k

Cite this

@article{7901f7e265c247b8ac3ba6ffe16863c4,

title = "Synthesis of meso-5-azaindolyl-appended Zn(II) porphyrins via Pd-catalyzed annulation",

abstract = "Pd-catalyzed annulation reaction of meso-hexynyl Zn(II) porphyrin with 4-amlno-3-lodopyrldlne efficiently provides meso-3-{5-azaindolyl)-substituted Zn(II) porphyrin as a major product, which assembles to form a slipped cofacial dimer by the complementary coordination of the pyridine molety to the Zn(II) center. 2-Iodoaniline and 2-Iodophenol also undergo this [3 + 2] annulation with the meso-hexynyl Zn(II) porphyrin to furnish meso-Indolyl- and benzofuranyl-substituted Zn(II) porphyrins, respectively.",

author = "Chihiro Maeda and Hiroshi Shinokubo and Atsuhiro Osuka",

year = "2007",

month = jun,

day = "21",

doi = "10.1021/ol070885k",

language = "English",

volume = "9",

pages = "2493--2496",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "13",

}

TY - JOUR

T1 - Synthesis of meso-5-azaindolyl-appended Zn(II) porphyrins via Pd-catalyzed annulation

AU - Maeda, Chihiro

AU - Shinokubo, Hiroshi

AU - Osuka, Atsuhiro

PY - 2007/6/21

Y1 - 2007/6/21

N2 - Pd-catalyzed annulation reaction of meso-hexynyl Zn(II) porphyrin with 4-amlno-3-lodopyrldlne efficiently provides meso-3-{5-azaindolyl)-substituted Zn(II) porphyrin as a major product, which assembles to form a slipped cofacial dimer by the complementary coordination of the pyridine molety to the Zn(II) center. 2-Iodoaniline and 2-Iodophenol also undergo this [3 + 2] annulation with the meso-hexynyl Zn(II) porphyrin to furnish meso-Indolyl- and benzofuranyl-substituted Zn(II) porphyrins, respectively.

AB - Pd-catalyzed annulation reaction of meso-hexynyl Zn(II) porphyrin with 4-amlno-3-lodopyrldlne efficiently provides meso-3-{5-azaindolyl)-substituted Zn(II) porphyrin as a major product, which assembles to form a slipped cofacial dimer by the complementary coordination of the pyridine molety to the Zn(II) center. 2-Iodoaniline and 2-Iodophenol also undergo this [3 + 2] annulation with the meso-hexynyl Zn(II) porphyrin to furnish meso-Indolyl- and benzofuranyl-substituted Zn(II) porphyrins, respectively.

UR - http://www.scopus.com/inward/record.url?scp=34547189132&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=34547189132&partnerID=8YFLogxK

U2 - 10.1021/ol070885k

DO - 10.1021/ol070885k

M3 - Article

C2 - 17518479

AN - SCOPUS:34547189132

SN - 1523-7060

VL - 9

SP - 2493

EP - 2496

JO - Organic Letters

JF - Organic Letters

IS - 13

ER -

Synthesis of meso-5-azaindolyl-appended Zn(II) porphyrins via Pd-catalyzed annulation

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this