New syntheses of tricyclic thiophenes and cyclic tetrathiophenes using transition-metal-catalyzed cyclization

S. M.Humayun Kabir; Mami Miura; Shigeru Sasaki; Genta Harada; Yoshiyuki Kuwatani; Masato Yoshida; Masahiko Iyoda

doi:10.3987/com-99-s86

New syntheses of tricyclic thiophenes and cyclic tetrathiophenes using transition-metal-catalyzed cyclization

S. M.Humayun Kabir, Mami Miura, Shigeru Sasaki, Genta Harada, Yoshiyuki Kuwatani, Masato Yoshida, Masahiko Iyoda

SCI - Chemistry

Tokyo Metropolitan University

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

56 Citations (Scopus)

Abstract

New synthetic methods for polycyclic thiophenes were developed. Thus, dithienothiophenes, cyclopentadithiophene, silacyclopentadithiophenes, and cyclooctatetrathiophenes were synthesized in moderate to good yields by using the CuCl₂-mediated cyclization of organocopper(I) and organozinc intermediates prepared from dilithio-derivatives with CuCN or ZnCl₂, respectively. A direct cyclization of bromothiophene derivatives with hexamethylditin in the presence of tetrakis(triphenylphosphine)palladium(0) also gave dithienothiophenes, cyclopenta-dithiophenes, and silacyclopentadithiophenes in good yields.

Original language	English
Pages (from-to)	761-774
Number of pages	14
Journal	Heterocycles
Volume	52
Issue number	2
DOIs	https://doi.org/10.3987/com-99-s86
Publication status	Published - 2000 Feb 1

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abstract = "New synthetic methods for polycyclic thiophenes were developed. Thus, dithienothiophenes, cyclopentadithiophene, silacyclopentadithiophenes, and cyclooctatetrathiophenes were synthesized in moderate to good yields by using the CuCl2-mediated cyclization of organocopper(I) and organozinc intermediates prepared from dilithio-derivatives with CuCN or ZnCl2, respectively. A direct cyclization of bromothiophene derivatives with hexamethylditin in the presence of tetrakis(triphenylphosphine)palladium(0) also gave dithienothiophenes, cyclopenta-dithiophenes, and silacyclopentadithiophenes in good yields.",

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T1 - New syntheses of tricyclic thiophenes and cyclic tetrathiophenes using transition-metal-catalyzed cyclization

AU - Kabir, S. M.Humayun

AU - Miura, Mami

AU - Sasaki, Shigeru

AU - Harada, Genta

AU - Kuwatani, Yoshiyuki

AU - Yoshida, Masato

AU - Iyoda, Masahiko

PY - 2000/2/1

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N2 - New synthetic methods for polycyclic thiophenes were developed. Thus, dithienothiophenes, cyclopentadithiophene, silacyclopentadithiophenes, and cyclooctatetrathiophenes were synthesized in moderate to good yields by using the CuCl2-mediated cyclization of organocopper(I) and organozinc intermediates prepared from dilithio-derivatives with CuCN or ZnCl2, respectively. A direct cyclization of bromothiophene derivatives with hexamethylditin in the presence of tetrakis(triphenylphosphine)palladium(0) also gave dithienothiophenes, cyclopenta-dithiophenes, and silacyclopentadithiophenes in good yields.

AB - New synthetic methods for polycyclic thiophenes were developed. Thus, dithienothiophenes, cyclopentadithiophene, silacyclopentadithiophenes, and cyclooctatetrathiophenes were synthesized in moderate to good yields by using the CuCl2-mediated cyclization of organocopper(I) and organozinc intermediates prepared from dilithio-derivatives with CuCN or ZnCl2, respectively. A direct cyclization of bromothiophene derivatives with hexamethylditin in the presence of tetrakis(triphenylphosphine)palladium(0) also gave dithienothiophenes, cyclopenta-dithiophenes, and silacyclopentadithiophenes in good yields.

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New syntheses of tricyclic thiophenes and cyclic tetrathiophenes using transition-metal-catalyzed cyclization

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