A cascade Suzuki-Miyaura/Diels-Alder protocol: exploring the bifunctional utility of vinyl Bpin

David L. Cain; Calum McLaughlin; John Molloy; Cameron Carpenter-Warren; Niall A. Anderson; Allan J. B. Watson

doi:10.1055/s-0037-1611228

A cascade Suzuki-Miyaura/Diels-Alder protocol: exploring the bifunctional utility of vinyl Bpin

David L. Cain, Calum McLaughlin, John Molloy, Cameron Carpenter-Warren, Niall A. Anderson, Allan J. B. Watson

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

Abstract

Cascade reactions are an important strategy in reaction design, allowing streamlining of chemical synthesis. Here we report a cascade Suzuki-Miyaura/Diels-Alder reaction, employing vinyl Bpin as a bifunctional reagent in two distinct roles: as an organoboron nucleophile for cross- coupling and as a Diels-Alder dienophile. Merging these two reactions enables a rapid and operationally simple synthesis of functionalized carbocycles in good yield. The effect of the organoboron subtype on Diels- Alder regioselectivity was investigated and post-synthetic modifications were carried out on a model substrate. The potential for a complementary Heck/Diels-Alder process was also assessed.

Original language	English
Pages (from-to)	787-791
Number of pages	5
Journal	Synlett
Volume	30
Issue number	7
Early online date	24 Oct 2018
DOIs	https://doi.org/10.1055/s-0037-1611228
Publication status	Published - Apr 2019

Keywords

Bpin
Cascade
Cross-coupling
Diels-Alder
Suzuki-Miyaura

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10.1055/s-0037-1611228

Watson Manuscript AAM
Copyright © 2018, Georg Thieme Verlag. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1055/s-0037-1611228
Accepted author manuscript, 551 KB

Cite this

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title = "A cascade Suzuki-Miyaura/Diels-Alder protocol: exploring the bifunctional utility of vinyl Bpin",

abstract = "Cascade reactions are an important strategy in reaction design, allowing streamlining of chemical synthesis. Here we report a cascade Suzuki-Miyaura/Diels-Alder reaction, employing vinyl Bpin as a bifunctional reagent in two distinct roles: as an organoboron nucleophile for cross- coupling and as a Diels-Alder dienophile. Merging these two reactions enables a rapid and operationally simple synthesis of functionalized carbocycles in good yield. The effect of the organoboron subtype on Diels- Alder regioselectivity was investigated and post-synthetic modifications were carried out on a model substrate. The potential for a complementary Heck/Diels-Alder process was also assessed.",

keywords = "Bpin, Cascade, Cross-coupling, Diels-Alder, Suzuki-Miyaura",

author = "Cain, {David L.} and Calum McLaughlin and John Molloy and Cameron Carpenter-Warren and Anderson, {Niall A.} and Watson, {Allan J. B.}",

note = "Funding: Industrial CASE studentship awarded from EPSRC and GlaxoSmithKline. The authors thank the EPSRC, GlaxoSmithKline, and the University of St Andrews for studentship funding (DLC), and the University of St Andrews and the EPSRC UK National Mass Spectrometry Facility at Swansea University for analyses.",

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doi = "10.1055/s-0037-1611228",

language = "English",

volume = "30",

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journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

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TY - JOUR

T1 - A cascade Suzuki-Miyaura/Diels-Alder protocol

T2 - exploring the bifunctional utility of vinyl Bpin

AU - Cain, David L.

AU - McLaughlin, Calum

AU - Molloy, John

AU - Carpenter-Warren, Cameron

AU - Anderson, Niall A.

AU - Watson, Allan J. B.

N1 - Funding: Industrial CASE studentship awarded from EPSRC and GlaxoSmithKline. The authors thank the EPSRC, GlaxoSmithKline, and the University of St Andrews for studentship funding (DLC), and the University of St Andrews and the EPSRC UK National Mass Spectrometry Facility at Swansea University for analyses.

PY - 2019/4

Y1 - 2019/4

N2 - Cascade reactions are an important strategy in reaction design, allowing streamlining of chemical synthesis. Here we report a cascade Suzuki-Miyaura/Diels-Alder reaction, employing vinyl Bpin as a bifunctional reagent in two distinct roles: as an organoboron nucleophile for cross- coupling and as a Diels-Alder dienophile. Merging these two reactions enables a rapid and operationally simple synthesis of functionalized carbocycles in good yield. The effect of the organoboron subtype on Diels- Alder regioselectivity was investigated and post-synthetic modifications were carried out on a model substrate. The potential for a complementary Heck/Diels-Alder process was also assessed.

AB - Cascade reactions are an important strategy in reaction design, allowing streamlining of chemical synthesis. Here we report a cascade Suzuki-Miyaura/Diels-Alder reaction, employing vinyl Bpin as a bifunctional reagent in two distinct roles: as an organoboron nucleophile for cross- coupling and as a Diels-Alder dienophile. Merging these two reactions enables a rapid and operationally simple synthesis of functionalized carbocycles in good yield. The effect of the organoboron subtype on Diels- Alder regioselectivity was investigated and post-synthetic modifications were carried out on a model substrate. The potential for a complementary Heck/Diels-Alder process was also assessed.

KW - Bpin

KW - Cascade

KW - Cross-coupling

KW - Diels-Alder

KW - Suzuki-Miyaura

UR - https://www.thieme-connect.de/media/synlett/EFirst/supmat/sup_st-2018-d0578-l_10-1055_s-0037-1611228.pdf

U2 - 10.1055/s-0037-1611228

DO - 10.1055/s-0037-1611228

M3 - Article

SN - 0936-5214

VL - 30

SP - 787

EP - 791

JO - Synlett

JF - Synlett

IS - 7

ER -

A cascade Suzuki-Miyaura/Diels-Alder protocol: exploring the bifunctional utility of vinyl Bpin

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Keywords

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