Pd(II)-Catalyzed [4 + 2] Heterocyclization Sequence for Polyheterocycle Generation

Elizabeth L. Glaisyer; Michael S. Watt; Kevin I. Booker-Milburn

doi:10.1021/acs.orglett.8b02543

Pd(II)-Catalyzed [4 + 2] Heterocyclization Sequence for Polyheterocycle Generation

Elizabeth L. Glaisyer, Michael S. Watt, Kevin I. Booker-Milburn^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

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Abstract

A new Pd(II)-catalyzed cascade sequence for the formation of polyheterocycles, from simple starting materials, is reported. The sequence is applicable to both indole and pyrrole substrates, and a range of substituents are tolerated. The reaction is thought to proceed by a Pd(II)-catalyzed C-H activated Heck reaction followed by a second Pd(II)-catalyzed aza-Wacker reaction with two Cu(II)-mediated Pd(0) turnovers per sequence. The sequence can be considered a formal [4 + 2] heterocyclization.

Original language	English
Pages (from-to)	5877-5880
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	18
Early online date	7 Sept 2018
DOIs	https://doi.org/10.1021/acs.orglett.8b02543
Publication status	Published - 21 Sept 2018

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@article{2928f5d1e4974496931472d14550c86a,

title = "Pd(II)-Catalyzed [4 + 2] Heterocyclization Sequence for Polyheterocycle Generation",

abstract = "A new Pd(II)-catalyzed cascade sequence for the formation of polyheterocycles, from simple starting materials, is reported. The sequence is applicable to both indole and pyrrole substrates, and a range of substituents are tolerated. The reaction is thought to proceed by a Pd(II)-catalyzed C-H activated Heck reaction followed by a second Pd(II)-catalyzed aza-Wacker reaction with two Cu(II)-mediated Pd(0) turnovers per sequence. The sequence can be considered a formal [4 + 2] heterocyclization.",

author = "Glaisyer, \{Elizabeth L.\} and Watt, \{Michael S.\} and Booker-Milburn, \{Kevin I.\}",

year = "2018",

month = sep,

day = "21",

doi = "10.1021/acs.orglett.8b02543",

language = "English",

volume = "20",

pages = "5877--5880",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "18",

}

TY - JOUR

T1 - Pd(II)-Catalyzed [4 + 2] Heterocyclization Sequence for Polyheterocycle Generation

AU - Glaisyer, Elizabeth L.

AU - Watt, Michael S.

AU - Booker-Milburn, Kevin I.

PY - 2018/9/21

Y1 - 2018/9/21

N2 - A new Pd(II)-catalyzed cascade sequence for the formation of polyheterocycles, from simple starting materials, is reported. The sequence is applicable to both indole and pyrrole substrates, and a range of substituents are tolerated. The reaction is thought to proceed by a Pd(II)-catalyzed C-H activated Heck reaction followed by a second Pd(II)-catalyzed aza-Wacker reaction with two Cu(II)-mediated Pd(0) turnovers per sequence. The sequence can be considered a formal [4 + 2] heterocyclization.

AB - A new Pd(II)-catalyzed cascade sequence for the formation of polyheterocycles, from simple starting materials, is reported. The sequence is applicable to both indole and pyrrole substrates, and a range of substituents are tolerated. The reaction is thought to proceed by a Pd(II)-catalyzed C-H activated Heck reaction followed by a second Pd(II)-catalyzed aza-Wacker reaction with two Cu(II)-mediated Pd(0) turnovers per sequence. The sequence can be considered a formal [4 + 2] heterocyclization.

UR - http://www.scopus.com/inward/record.url?scp=85053534369&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.8b02543

DO - 10.1021/acs.orglett.8b02543

M3 - Article (Academic Journal)

C2 - 30192546

AN - SCOPUS:85053534369

SN - 1523-7060

VL - 20

SP - 5877

EP - 5880

JO - Organic Letters

JF - Organic Letters

IS - 18

ER -

Pd(II)-Catalyzed [4 + 2] Heterocyclization Sequence for Polyheterocycle Generation

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The Development of Pd(II)-Catalysed C–H Activation Cascades for the Synthesis of Polyheterocycles

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Pd(II)-Catalyzed [4 + 2] Heterocyclization Sequence for Polyheterocycle Generation

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The Development of Pd(II)-Catalysed C–H Activation Cascades for the Synthesis of Polyheterocycles

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