Metal-free access to 3-allyl-2-alkoxychromanonesviaphosphine-catalyzed alkoxy allylation of chromones with MBH carbonates and alcohols

Ling Meng; Xiaoyong Chang; Zhenyang Lin; Jun Wang

doi:10.1039/D1OB00215E

Metal-free access to 3-allyl-2-alkoxychromanonesviaphosphine-catalyzed alkoxy allylation of chromones with MBH carbonates and alcohols

Ling Meng
, Xiaoyong Chang
, Zhenyang Lin^*
, Jun Wang^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

6 Citations (Scopus)

Abstract

A metal-free access to 3-allyl-2-alkoxychromanones by PPh₃-catalyzed alkoxy allylation of chromones with MBH carbonates and alcohols is described. This reaction is performed under mild conditions and it shows good functional group tolerance, providing a series of functionalized chromanones in moderate to high yields with excellent diastereoselectivities. Deuterium-labeling experiments to probe a possible mechanism and scale-up reaction were also conducted.

Original language	English
Pages (from-to)	2663-2667
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	19
Issue number	12
DOIs	https://doi.org/10.1039/D1OB00215E
Publication status	Published - 28 Mar 2021

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title = "Metal-free access to 3-allyl-2-alkoxychromanonesviaphosphine-catalyzed alkoxy allylation of chromones with MBH carbonates and alcohols",

abstract = "A metal-free access to 3-allyl-2-alkoxychromanones by PPh3-catalyzed alkoxy allylation of chromones with MBH carbonates and alcohols is described. This reaction is performed under mild conditions and it shows good functional group tolerance, providing a series of functionalized chromanones in moderate to high yields with excellent diastereoselectivities. Deuterium-labeling experiments to probe a possible mechanism and scale-up reaction were also conducted.",

author = "Ling Meng and Xiaoyong Chang and Zhenyang Lin and Jun Wang",

note = "Funding Information: We gratefully acknowledge Shenzhen Overseas High-level Talents Innovation Plan of Technical Innovation Project (KQJSCX20180319114439973) for financial support.",

year = "2021",

month = mar,

day = "28",

doi = "10.1039/D1OB00215E",

language = "English",

volume = "19",

pages = "2663--2667",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "12",

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TY - JOUR

T1 - Metal-free access to 3-allyl-2-alkoxychromanonesviaphosphine-catalyzed alkoxy allylation of chromones with MBH carbonates and alcohols

AU - Meng, Ling

AU - Chang, Xiaoyong

AU - Lin, Zhenyang

AU - Wang, Jun

N1 - Funding Information: We gratefully acknowledge Shenzhen Overseas High-level Talents Innovation Plan of Technical Innovation Project (KQJSCX20180319114439973) for financial support.

PY - 2021/3/28

Y1 - 2021/3/28

N2 - A metal-free access to 3-allyl-2-alkoxychromanones by PPh3-catalyzed alkoxy allylation of chromones with MBH carbonates and alcohols is described. This reaction is performed under mild conditions and it shows good functional group tolerance, providing a series of functionalized chromanones in moderate to high yields with excellent diastereoselectivities. Deuterium-labeling experiments to probe a possible mechanism and scale-up reaction were also conducted.

AB - A metal-free access to 3-allyl-2-alkoxychromanones by PPh3-catalyzed alkoxy allylation of chromones with MBH carbonates and alcohols is described. This reaction is performed under mild conditions and it shows good functional group tolerance, providing a series of functionalized chromanones in moderate to high yields with excellent diastereoselectivities. Deuterium-labeling experiments to probe a possible mechanism and scale-up reaction were also conducted.

UR - https://www.scopus.com/pages/publications/85103516477

U2 - 10.1039/D1OB00215E

DO - 10.1039/D1OB00215E

M3 - Journal article

C2 - 33688906

AN - SCOPUS:85103516477

SN - 1477-0520

VL - 19

SP - 2663

EP - 2667

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 12

ER -

Metal-free access to 3-allyl-2-alkoxychromanonesviaphosphine-catalyzed alkoxy allylation of chromones with MBH carbonates and alcohols

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