THE SYNTHESIS OF BRIDGED-RING CARBOCYCLES AND HETEROCYCLES VIA PALLADIUM CATALYZED REGIOSPECIFIC CYCLIZATION REACTIONS

R GRIGG; [No Value] SANTHAKUMAR; Seshadri SRIDHARAN; P STEVENSON; A TEASDALE; M THORNTONPETT; T WORAKUN

THE SYNTHESIS OF BRIDGED-RING CARBOCYCLES AND HETEROCYCLES VIA PALLADIUM CATALYZED REGIOSPECIFIC CYCLIZATION REACTIONS

R GRIGG^*, [No Value] SANTHAKUMAR, Seshadri SRIDHARAN, P STEVENSON, A TEASDALE, M THORNTONPETT, T WORAKUN

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

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

65 Citations (Scopus)

Abstract

A catalyst system comprising 10 mol % (Pd(OAc) and 20 mol % PPh3 effects the cyclisation of aryl halides onto proximate alkenes via 5-, 6-, and 7-exo-trig, and 7-endo-trig processes giving a variety of bridged-ring carbo- and hetero-cycles in excellent yield. Double bond isomerisation in the product is rarely encountered and may be suppressed by the addition of Tl(1) salts. One example of diastereospecific bis-cyclisation is given and the crystal structure of 1-aza-2-sulphonyl-3,4-benzobicyclo[3.2.1]nona-6-ene is reported.

Original language	English
Pages (from-to)	9703-9720
Number of pages	18
Journal	Tetrahedron
Volume	47
Issue number	46
Publication status	Published - 25 Nov 1991

Keywords

PALLADIUM CATALYSIS
BRIDGED-RING CYCLIZATION
METAL-PROMOTED CYCLIZATION
ANION CAPTURE PROCESSES
POLYENE CYCLIZATIONS
CRYSTAL-STRUCTURE
SILVER-NITRATE
ARYLATION
VINYLATION
COMPLEXES
HALIDES
ALKENES

Cite this

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title = "THE SYNTHESIS OF BRIDGED-RING CARBOCYCLES AND HETEROCYCLES VIA PALLADIUM CATALYZED REGIOSPECIFIC CYCLIZATION REACTIONS",

abstract = "A catalyst system comprising 10 mol % (Pd(OAc) and 20 mol % PPh3 effects the cyclisation of aryl halides onto proximate alkenes via 5-, 6-, and 7-exo-trig, and 7-endo-trig processes giving a variety of bridged-ring carbo- and hetero-cycles in excellent yield. Double bond isomerisation in the product is rarely encountered and may be suppressed by the addition of Tl(1) salts. One example of diastereospecific bis-cyclisation is given and the crystal structure of 1-aza-2-sulphonyl-3,4-benzobicyclo[3.2.1]nona-6-ene is reported.",

keywords = "PALLADIUM CATALYSIS, BRIDGED-RING CYCLIZATION, METAL-PROMOTED CYCLIZATION, ANION CAPTURE PROCESSES, POLYENE CYCLIZATIONS, CRYSTAL-STRUCTURE, SILVER-NITRATE, ARYLATION, VINYLATION, COMPLEXES, HALIDES, ALKENES",

author = "R GRIGG and SANTHAKUMAR, {[No Value]} and Seshadri SRIDHARAN and P STEVENSON and A TEASDALE and M THORNTONPETT and T WORAKUN",

year = "1991",

month = nov,

day = "25",

language = "English",

volume = "47",

pages = "9703--9720",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "46",

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TY - JOUR

T1 - THE SYNTHESIS OF BRIDGED-RING CARBOCYCLES AND HETEROCYCLES VIA PALLADIUM CATALYZED REGIOSPECIFIC CYCLIZATION REACTIONS

AU - GRIGG, R

AU - SANTHAKUMAR, [No Value]

AU - SRIDHARAN, Seshadri

AU - STEVENSON, P

AU - TEASDALE, A

AU - THORNTONPETT, M

AU - WORAKUN, T

PY - 1991/11/25

Y1 - 1991/11/25

N2 - A catalyst system comprising 10 mol % (Pd(OAc) and 20 mol % PPh3 effects the cyclisation of aryl halides onto proximate alkenes via 5-, 6-, and 7-exo-trig, and 7-endo-trig processes giving a variety of bridged-ring carbo- and hetero-cycles in excellent yield. Double bond isomerisation in the product is rarely encountered and may be suppressed by the addition of Tl(1) salts. One example of diastereospecific bis-cyclisation is given and the crystal structure of 1-aza-2-sulphonyl-3,4-benzobicyclo[3.2.1]nona-6-ene is reported.

AB - A catalyst system comprising 10 mol % (Pd(OAc) and 20 mol % PPh3 effects the cyclisation of aryl halides onto proximate alkenes via 5-, 6-, and 7-exo-trig, and 7-endo-trig processes giving a variety of bridged-ring carbo- and hetero-cycles in excellent yield. Double bond isomerisation in the product is rarely encountered and may be suppressed by the addition of Tl(1) salts. One example of diastereospecific bis-cyclisation is given and the crystal structure of 1-aza-2-sulphonyl-3,4-benzobicyclo[3.2.1]nona-6-ene is reported.

KW - PALLADIUM CATALYSIS

KW - BRIDGED-RING CYCLIZATION

KW - METAL-PROMOTED CYCLIZATION

KW - ANION CAPTURE PROCESSES

KW - POLYENE CYCLIZATIONS

KW - CRYSTAL-STRUCTURE

KW - SILVER-NITRATE

KW - ARYLATION

KW - VINYLATION

KW - COMPLEXES

KW - HALIDES

KW - ALKENES

M3 - Article

SN - 0040-4020

VL - 47

SP - 9703

EP - 9720

JO - Tetrahedron

JF - Tetrahedron

IS - 46

ER -

THE SYNTHESIS OF BRIDGED-RING CARBOCYCLES AND HETEROCYCLES VIA PALLADIUM CATALYZED REGIOSPECIFIC CYCLIZATION REACTIONS

Abstract

Keywords

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