Elongated phosphoranes by C–C coupling of haloaroylmethylidenetriphenylphosphoranes: Synthesis and applications

Thies Thiemann; Kuniharu Umeno; Jian Wang; Yumiko Tabuchi; Kazuya Arima; Masataka Watanabe; Yasuko Tanaka; Hideki Gorohmaru; Shuntaro Mataka

doi:10.1039/b202745n

Elongated phosphoranes by C–C coupling of haloaroylmethylidenetriphenylphosphoranes: Synthesis and applications

Thies Thiemann
, Kuniharu Umeno
, Jian Wang
, Yumiko Tabuchi
, Kazuya Arima
, Masataka Watanabe
, Yasuko Tanaka
, Hideki Gorohmaru
, Shuntaro Mataka

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

24 Citations (Scopus)

Abstract

Haloaroylmethylidenephosphoranes 3 can be subjected to Pd(0) mediated C–C coupling reactions to yield diaryl-, arylhetaryl-, dihetaryl, arylethenylaryl/hetaryl- and arylethynylaryl/hetaryl-carbonylmethylidenephosphoranes 4–9. Suzuki–Kumada reactions can also be run in a one-step procedure from (haloaroylmethyl)triphenylphosphonium bromides 2. Compounds 4–9 are air-stable phosphoranes which undergo formal Wittig-olefination reactions with aldehydes 10 under benzoic acid catalysis. C–C coupling reaction and Wittig olefination can also be performed in a one-step procedure. Preliminary experiments have been performed to carry out the synthesis on a solid support. Applications to the chain elongation and functionalisation of the chain terminus in a C-7 substituted estra-1,3,5(10)-triene 14 and a C-16 substituted estra-1,3,5(10),6-tetraene 12 are shown.

Original language	English
Pages (from-to)	2090-2110
Number of pages	21
Journal	Journal of the Chemical Society. Perkin Transactions 1
Volume	2
Issue number	18
DOIs	https://doi.org/10.1039/b202745n
Publication status	Published - Mar 18 2002
Externally published	Yes

ASJC Scopus subject areas

General Chemistry

Access to Document

10.1039/b202745n

Cite this

@article{83c5adb1a8a54e32845e72ad23b686a9,

title = "Elongated phosphoranes by C–C coupling of haloaroylmethylidenetriphenylphosphoranes: Synthesis and applications",

abstract = "Haloaroylmethylidenephosphoranes 3 can be subjected to Pd(0) mediated C–C coupling reactions to yield diaryl-, arylhetaryl-, dihetaryl, arylethenylaryl/hetaryl- and arylethynylaryl/hetaryl-carbonylmethylidenephosphoranes 4–9. Suzuki–Kumada reactions can also be run in a one-step procedure from (haloaroylmethyl)triphenylphosphonium bromides 2. Compounds 4–9 are air-stable phosphoranes which undergo formal Wittig-olefination reactions with aldehydes 10 under benzoic acid catalysis. C–C coupling reaction and Wittig olefination can also be performed in a one-step procedure. Preliminary experiments have been performed to carry out the synthesis on a solid support. Applications to the chain elongation and functionalisation of the chain terminus in a C-7 substituted estra-1,3,5(10)-triene 14 and a C-16 substituted estra-1,3,5(10),6-tetraene 12 are shown.",

author = "Thies Thiemann and Kuniharu Umeno and Jian Wang and Yumiko Tabuchi and Kazuya Arima and Masataka Watanabe and Yasuko Tanaka and Hideki Gorohmaru and Shuntaro Mataka",

year = "2002",

month = mar,

day = "18",

doi = "10.1039/b202745n",

language = "English",

volume = "2",

pages = "2090--2110",

journal = "Journal of the Chemical Society. Perkin Transactions 1",

issn = "1472-7781",

publisher = "Chemical Society",

number = "18",

}

TY - JOUR

T1 - Elongated phosphoranes by C–C coupling of haloaroylmethylidenetriphenylphosphoranes

T2 - Synthesis and applications

AU - Thiemann, Thies

AU - Umeno, Kuniharu

AU - Wang, Jian

AU - Tabuchi, Yumiko

AU - Arima, Kazuya

AU - Watanabe, Masataka

AU - Tanaka, Yasuko

AU - Gorohmaru, Hideki

AU - Mataka, Shuntaro

PY - 2002/3/18

Y1 - 2002/3/18

N2 - Haloaroylmethylidenephosphoranes 3 can be subjected to Pd(0) mediated C–C coupling reactions to yield diaryl-, arylhetaryl-, dihetaryl, arylethenylaryl/hetaryl- and arylethynylaryl/hetaryl-carbonylmethylidenephosphoranes 4–9. Suzuki–Kumada reactions can also be run in a one-step procedure from (haloaroylmethyl)triphenylphosphonium bromides 2. Compounds 4–9 are air-stable phosphoranes which undergo formal Wittig-olefination reactions with aldehydes 10 under benzoic acid catalysis. C–C coupling reaction and Wittig olefination can also be performed in a one-step procedure. Preliminary experiments have been performed to carry out the synthesis on a solid support. Applications to the chain elongation and functionalisation of the chain terminus in a C-7 substituted estra-1,3,5(10)-triene 14 and a C-16 substituted estra-1,3,5(10),6-tetraene 12 are shown.

AB - Haloaroylmethylidenephosphoranes 3 can be subjected to Pd(0) mediated C–C coupling reactions to yield diaryl-, arylhetaryl-, dihetaryl, arylethenylaryl/hetaryl- and arylethynylaryl/hetaryl-carbonylmethylidenephosphoranes 4–9. Suzuki–Kumada reactions can also be run in a one-step procedure from (haloaroylmethyl)triphenylphosphonium bromides 2. Compounds 4–9 are air-stable phosphoranes which undergo formal Wittig-olefination reactions with aldehydes 10 under benzoic acid catalysis. C–C coupling reaction and Wittig olefination can also be performed in a one-step procedure. Preliminary experiments have been performed to carry out the synthesis on a solid support. Applications to the chain elongation and functionalisation of the chain terminus in a C-7 substituted estra-1,3,5(10)-triene 14 and a C-16 substituted estra-1,3,5(10),6-tetraene 12 are shown.

UR - https://www.scopus.com/pages/publications/0036026242

UR - https://www.scopus.com/pages/publications/0036026242#tab=citedBy

U2 - 10.1039/b202745n

DO - 10.1039/b202745n

M3 - Article

AN - SCOPUS:0036026242

SN - 1472-7781

VL - 2

SP - 2090

EP - 2110

JO - Journal of the Chemical Society. Perkin Transactions 1

JF - Journal of the Chemical Society. Perkin Transactions 1

IS - 18

ER -

Elongated phosphoranes by C–C coupling of haloaroylmethylidenetriphenylphosphoranes: Synthesis and applications

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this