Synthesis of 3,3-disubstituted heterocycles by Pd-catalyzed arylallylation of unactivated alkenes

David Phillips; Joanne F.M. Hewitt; David J. France

doi:10.1021/acsomega.8b01021

Synthesis of 3,3-disubstituted heterocycles by Pd-catalyzed arylallylation of unactivated alkenes

David Phillips
, Joanne F.M. Hewitt
, David J. France

Drug Discovery Unit

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

6 Citations (Scopus)

115 Downloads (Pure)

Abstract

Finding new methods of carbon-carbon bond formation is a key goal in expanding current methodology for heterocycle formation. Because of their inherently nonplanar shape, new methods of forming sp³-rich scaffolds are of particular importance. Although there are methods for combining heterocyclization and formation of new sp³-sp³ carbon-carbon bonds, these form the carbon-heteroatom bond rather than a carbon-carbon bond of the heterocycle. Here, we show a new alkene arylallylation reaction that generates a heterocycle with concomitant formation of two new carbon-carbon bonds. Furthermore, we demonstrate that this process occurs through an isohypsic (redox neutral) mechanism. Overall, this carboallylation reaction gives a new route to the synthesis of 3,3-disubstituted heterocycles.

Original language	English
Pages (from-to)	8451-8459
Number of pages	9
Journal	ACS Omega
Volume	3
Issue number	7
DOIs	https://doi.org/10.1021/acsomega.8b01021
Publication status	Published - 31 Jul 2018

ASJC Scopus subject areas

General Chemistry
General Chemical Engineering

Access to Document

10.1021/acsomega.8b01021Licence: CC BY

Final Published VersionFinal published version, 1.99 MBLicence: CC BY

Cite this

@article{4fb9a3974f4d49f09712261ebabf4932,

title = "Synthesis of 3,3-disubstituted heterocycles by Pd-catalyzed arylallylation of unactivated alkenes",

abstract = "Finding new methods of carbon-carbon bond formation is a key goal in expanding current methodology for heterocycle formation. Because of their inherently nonplanar shape, new methods of forming sp3-rich scaffolds are of particular importance. Although there are methods for combining heterocyclization and formation of new sp3-sp3 carbon-carbon bonds, these form the carbon-heteroatom bond rather than a carbon-carbon bond of the heterocycle. Here, we show a new alkene arylallylation reaction that generates a heterocycle with concomitant formation of two new carbon-carbon bonds. Furthermore, we demonstrate that this process occurs through an isohypsic (redox neutral) mechanism. Overall, this carboallylation reaction gives a new route to the synthesis of 3,3-disubstituted heterocycles.",

author = "David Phillips and Hewitt, \{Joanne F.M.\} and France, \{David J.\}",

note = "Funding Information: Funding from the University of Glasgow and the EPSRC (award ref: EP/I027165/1) is gratefully acknowledged. Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

month = jul,

day = "31",

doi = "10.1021/acsomega.8b01021",

language = "English",

volume = "3",

pages = "8451--8459",

journal = "ACS Omega",

issn = "2470-1343",

publisher = "American Chemical Society",

number = "7",

}

TY - JOUR

T1 - Synthesis of 3,3-disubstituted heterocycles by Pd-catalyzed arylallylation of unactivated alkenes

AU - Phillips, David

AU - Hewitt, Joanne F.M.

AU - France, David J.

PY - 2018/7/31

Y1 - 2018/7/31

N2 - Finding new methods of carbon-carbon bond formation is a key goal in expanding current methodology for heterocycle formation. Because of their inherently nonplanar shape, new methods of forming sp3-rich scaffolds are of particular importance. Although there are methods for combining heterocyclization and formation of new sp3-sp3 carbon-carbon bonds, these form the carbon-heteroatom bond rather than a carbon-carbon bond of the heterocycle. Here, we show a new alkene arylallylation reaction that generates a heterocycle with concomitant formation of two new carbon-carbon bonds. Furthermore, we demonstrate that this process occurs through an isohypsic (redox neutral) mechanism. Overall, this carboallylation reaction gives a new route to the synthesis of 3,3-disubstituted heterocycles.

AB - Finding new methods of carbon-carbon bond formation is a key goal in expanding current methodology for heterocycle formation. Because of their inherently nonplanar shape, new methods of forming sp3-rich scaffolds are of particular importance. Although there are methods for combining heterocyclization and formation of new sp3-sp3 carbon-carbon bonds, these form the carbon-heteroatom bond rather than a carbon-carbon bond of the heterocycle. Here, we show a new alkene arylallylation reaction that generates a heterocycle with concomitant formation of two new carbon-carbon bonds. Furthermore, we demonstrate that this process occurs through an isohypsic (redox neutral) mechanism. Overall, this carboallylation reaction gives a new route to the synthesis of 3,3-disubstituted heterocycles.

UR - https://www.scopus.com/pages/publications/85059646085

U2 - 10.1021/acsomega.8b01021

DO - 10.1021/acsomega.8b01021

M3 - Article

AN - SCOPUS:85059646085

SN - 2470-1343

VL - 3

SP - 8451

EP - 8459

JO - ACS Omega

JF - ACS Omega

IS - 7

ER -

Synthesis of 3,3-disubstituted heterocycles by Pd-catalyzed arylallylation of unactivated alkenes

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this