NHC-Copper-Catalyzed Tandem Hydrocupration and Allylation of Alkenyl Boronates

Won Jun Jang; Jung Tae Han; Jaesook Yun

doi:10.1055/s-0036-1588811

NHC-Copper-Catalyzed Tandem Hydrocupration and Allylation of Alkenyl Boronates

Won Jun Jang, Jung Tae Han, Jaesook Yun

Department of Chemistry & Nanoscience

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

11 Scopus citations

Abstract

A tandem hydrocupration/allylation of alkenyl boronates efficiently proceeds with NHC-copper catalysts using hydrosilane and allyl phosphate as reagents. In the presence of IMes-Cu catalyst, the allylation of in situ generated Β-α-copper intermediates smoothly occurs to give homoallylic boronates in high yields, despite competitive side reaction pathways. Mono- and disubstituted alkenyl boronates were effective in the reaction with terminal allyl phosphates, but trisubstituted substrates showed limited reactivity.

Original language	English
Pages (from-to)	4753-4758
Number of pages	6
Journal	Synthesis (Germany)
Volume	49
Issue number	21
DOIs	https://doi.org/10.1055/s-0036-1588811
State	Published - 2 Nov 2017

Bibliographical note

Funding Information:
National Research Foundation of Korea grant (NRF-2016R1A2B4011719) funded by the Korean government (MEST).

Publisher Copyright:
© Georg Thieme Verlag Stuttgart New York.

Keywords

allylic substitution
copper
homoallylic boronates
hydrocupration
N-heterocyclic carbenes
tandem reaction

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title = "NHC-Copper-Catalyzed Tandem Hydrocupration and Allylation of Alkenyl Boronates",

abstract = "A tandem hydrocupration/allylation of alkenyl boronates efficiently proceeds with NHC-copper catalysts using hydrosilane and allyl phosphate as reagents. In the presence of IMes-Cu catalyst, the allylation of in situ generated Β-α-copper intermediates smoothly occurs to give homoallylic boronates in high yields, despite competitive side reaction pathways. Mono- and disubstituted alkenyl boronates were effective in the reaction with terminal allyl phosphates, but trisubstituted substrates showed limited reactivity.",

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author = "Jang, {Won Jun} and Han, {Jung Tae} and Jaesook Yun",

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T1 - NHC-Copper-Catalyzed Tandem Hydrocupration and Allylation of Alkenyl Boronates

AU - Jang, Won Jun

AU - Han, Jung Tae

AU - Yun, Jaesook

N1 - Funding Information: National Research Foundation of Korea grant (NRF-2016R1A2B4011719) funded by the Korean government (MEST). Publisher Copyright: © Georg Thieme Verlag Stuttgart New York.

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Y1 - 2017/11/2

N2 - A tandem hydrocupration/allylation of alkenyl boronates efficiently proceeds with NHC-copper catalysts using hydrosilane and allyl phosphate as reagents. In the presence of IMes-Cu catalyst, the allylation of in situ generated Β-α-copper intermediates smoothly occurs to give homoallylic boronates in high yields, despite competitive side reaction pathways. Mono- and disubstituted alkenyl boronates were effective in the reaction with terminal allyl phosphates, but trisubstituted substrates showed limited reactivity.

AB - A tandem hydrocupration/allylation of alkenyl boronates efficiently proceeds with NHC-copper catalysts using hydrosilane and allyl phosphate as reagents. In the presence of IMes-Cu catalyst, the allylation of in situ generated Β-α-copper intermediates smoothly occurs to give homoallylic boronates in high yields, despite competitive side reaction pathways. Mono- and disubstituted alkenyl boronates were effective in the reaction with terminal allyl phosphates, but trisubstituted substrates showed limited reactivity.

KW - allylic substitution

KW - copper

KW - homoallylic boronates

KW - hydrocupration

KW - N-heterocyclic carbenes

KW - tandem reaction

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DO - 10.1055/s-0036-1588811

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IS - 21

ER -

NHC-Copper-Catalyzed Tandem Hydrocupration and Allylation of Alkenyl Boronates

Abstract

Bibliographical note

Keywords

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