Palladium catalysed tandem cyclisation - Anion capture processes .2. Cyclisation onto alkynes or allenes with hydride capture.

R Grigg; Sabarinathan Loganathan; Seshadri Sridharan; P Stevenson; S Sukirthalingam; T Worakun

Palladium catalysed tandem cyclisation - Anion capture processes .2. Cyclisation onto alkynes or allenes with hydride capture.

R Grigg^*, Sabarinathan Loganathan, Seshadri Sridharan, P Stevenson, S Sukirthalingam, T Worakun

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

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

77 Citations (Scopus)

Abstract

A wide range of palladium catalysed regio- and stereo-specific 5-, 6- and 7-exo-dig mono-, bis- and tris-cyclisation processes of aryl and vinyl halides and allylic acetates are described. The mono- and bis-cyclisation processes terminate in hydride capture from piperidine-formic acid or sodium formate. Addition of TI2CO3 results in alkyne-allene isomerisation and leads, after cyclisation, to 1,3-dienes which give Diels-Alder adducts in good yield. Copyright (C) 1996 Elsevier Science Ltd

Original language	English
Pages (from-to)	11479-11502
Number of pages	24
Journal	Tetrahedron
Volume	52
Issue number	35
Publication status	Published - 26 Aug 1996
Event	1st International Symposium on Cascade Reactions - LEEDS, United Kingdom Duration: 01 Jan 1994 → …

Keywords

FUNCTIONALLY-SUBSTITUTED ARYL
INTRAMOLECULAR HECK REACTIONS
REGIOSPECIFIC CYCLIZATION
DEHYDROGENATION ROUTE
COUPLING REACTION
EXCHANGE-REACTION
INTERNAL ALKYNES
TERTIARY-AMINES
ALLYLIC AMINES
ION CAPTURE

Cite this

@article{497d5a8d9082464b9537a9167d18a12d,

title = "Palladium catalysed tandem cyclisation - Anion capture processes .2. Cyclisation onto alkynes or allenes with hydride capture.",

abstract = "A wide range of palladium catalysed regio- and stereo-specific 5-, 6- and 7-exo-dig mono-, bis- and tris-cyclisation processes of aryl and vinyl halides and allylic acetates are described. The mono- and bis-cyclisation processes terminate in hydride capture from piperidine-formic acid or sodium formate. Addition of TI2CO3 results in alkyne-allene isomerisation and leads, after cyclisation, to 1,3-dienes which give Diels-Alder adducts in good yield. Copyright (C) 1996 Elsevier Science Ltd",

keywords = "FUNCTIONALLY-SUBSTITUTED ARYL, INTRAMOLECULAR HECK REACTIONS, REGIOSPECIFIC CYCLIZATION, DEHYDROGENATION ROUTE, COUPLING REACTION, EXCHANGE-REACTION, INTERNAL ALKYNES, TERTIARY-AMINES, ALLYLIC AMINES, ION CAPTURE",

author = "R Grigg and Sabarinathan Loganathan and Seshadri Sridharan and P Stevenson and S Sukirthalingam and T Worakun",

year = "1996",

month = aug,

day = "26",

language = "English",

volume = "52",

pages = "11479--11502",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "35",

note = "1st International Symposium on Cascade Reactions ; Conference date: 01-01-1994",

}

TY - JOUR

T1 - Palladium catalysed tandem cyclisation - Anion capture processes .2. Cyclisation onto alkynes or allenes with hydride capture.

AU - Grigg, R

AU - Loganathan, Sabarinathan

AU - Sridharan, Seshadri

AU - Stevenson, P

AU - Sukirthalingam, S

AU - Worakun, T

PY - 1996/8/26

Y1 - 1996/8/26

N2 - A wide range of palladium catalysed regio- and stereo-specific 5-, 6- and 7-exo-dig mono-, bis- and tris-cyclisation processes of aryl and vinyl halides and allylic acetates are described. The mono- and bis-cyclisation processes terminate in hydride capture from piperidine-formic acid or sodium formate. Addition of TI2CO3 results in alkyne-allene isomerisation and leads, after cyclisation, to 1,3-dienes which give Diels-Alder adducts in good yield. Copyright (C) 1996 Elsevier Science Ltd

AB - A wide range of palladium catalysed regio- and stereo-specific 5-, 6- and 7-exo-dig mono-, bis- and tris-cyclisation processes of aryl and vinyl halides and allylic acetates are described. The mono- and bis-cyclisation processes terminate in hydride capture from piperidine-formic acid or sodium formate. Addition of TI2CO3 results in alkyne-allene isomerisation and leads, after cyclisation, to 1,3-dienes which give Diels-Alder adducts in good yield. Copyright (C) 1996 Elsevier Science Ltd

KW - FUNCTIONALLY-SUBSTITUTED ARYL

KW - INTRAMOLECULAR HECK REACTIONS

KW - REGIOSPECIFIC CYCLIZATION

KW - DEHYDROGENATION ROUTE

KW - COUPLING REACTION

KW - EXCHANGE-REACTION

KW - INTERNAL ALKYNES

KW - TERTIARY-AMINES

KW - ALLYLIC AMINES

KW - ION CAPTURE

M3 - Article

VL - 52

SP - 11479

EP - 11502

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 35

T2 - 1st International Symposium on Cascade Reactions

Y2 - 1 January 1994

ER -