Boron trihalide mediated haloallylation of aryl aldehydes and its application to the preparation of (E)-1,3-dienes

Michael P. Quinn, Min Liang Yao, Li Yong, George Kabalka

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

In the presence of boron trihalides, aryl aldehydes couple readily with allylmetals to afford haloallylated products. The reactions tolerate a variety of functional groups. Simple aqueous workup of haloallylation reactions, followed by treatment with 1,8-diazabicyclo[5.4.0]undec-7-ene, provides a straightforward route to synthetically useful (E)-1,3-dienes. The mild reaction conditions, readily available starting materials, and high stereoselectivity make this two-step (E)-1,3-diene synthesis quite attractive.

Original languageEnglish (US)
Article numberM81011SS
Pages (from-to)3815-3820
Number of pages6
JournalSynthesis
Issue number23
DOIs
StatePublished - Oct 21 2011

Fingerprint

Stereoselectivity
Boron
Aldehydes
Functional groups
1,8-diazabicyclo(5.4.0)undec-7-ene

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

Cite this

Boron trihalide mediated haloallylation of aryl aldehydes and its application to the preparation of (E)-1,3-dienes. / Quinn, Michael P.; Yao, Min Liang; Yong, Li; Kabalka, George.

In: Synthesis, No. 23, M81011SS, 21.10.2011, p. 3815-3820.

Research output: Contribution to journalArticle

@article{44446da079d9478397a80b9a2bf1c8a0,
title = "Boron trihalide mediated haloallylation of aryl aldehydes and its application to the preparation of (E)-1,3-dienes",
abstract = "In the presence of boron trihalides, aryl aldehydes couple readily with allylmetals to afford haloallylated products. The reactions tolerate a variety of functional groups. Simple aqueous workup of haloallylation reactions, followed by treatment with 1,8-diazabicyclo[5.4.0]undec-7-ene, provides a straightforward route to synthetically useful (E)-1,3-dienes. The mild reaction conditions, readily available starting materials, and high stereoselectivity make this two-step (E)-1,3-diene synthesis quite attractive.",
author = "Quinn, {Michael P.} and Yao, {Min Liang} and Li Yong and George Kabalka",
year = "2011",
month = "10",
day = "21",
doi = "10.1055/s-0031-1289304",
language = "English (US)",
pages = "3815--3820",
journal = "Synthesis",
issn = "0039-7881",
publisher = "Georg Thieme Verlag",
number = "23",

}

TY - JOUR

T1 - Boron trihalide mediated haloallylation of aryl aldehydes and its application to the preparation of (E)-1,3-dienes

AU - Quinn, Michael P.

AU - Yao, Min Liang

AU - Yong, Li

AU - Kabalka, George

PY - 2011/10/21

Y1 - 2011/10/21

N2 - In the presence of boron trihalides, aryl aldehydes couple readily with allylmetals to afford haloallylated products. The reactions tolerate a variety of functional groups. Simple aqueous workup of haloallylation reactions, followed by treatment with 1,8-diazabicyclo[5.4.0]undec-7-ene, provides a straightforward route to synthetically useful (E)-1,3-dienes. The mild reaction conditions, readily available starting materials, and high stereoselectivity make this two-step (E)-1,3-diene synthesis quite attractive.

AB - In the presence of boron trihalides, aryl aldehydes couple readily with allylmetals to afford haloallylated products. The reactions tolerate a variety of functional groups. Simple aqueous workup of haloallylation reactions, followed by treatment with 1,8-diazabicyclo[5.4.0]undec-7-ene, provides a straightforward route to synthetically useful (E)-1,3-dienes. The mild reaction conditions, readily available starting materials, and high stereoselectivity make this two-step (E)-1,3-diene synthesis quite attractive.

UR - http://www.scopus.com/inward/record.url?scp=81855170183&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=81855170183&partnerID=8YFLogxK

U2 - 10.1055/s-0031-1289304

DO - 10.1055/s-0031-1289304

M3 - Article

SP - 3815

EP - 3820

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 23

M1 - M81011SS

ER -