Palladium-Catalyzed Allenylation/6π-Electrocyclization and 1,3-Hydrogen Migration: an Access to Naphtho[1,2-b]furans

Chengyu Wang; Yu Han; Mengyuan Li; Xuemei Zhou; Lingkai Kong; Yanzhong Li

doi:10.1002/ejoc.201901604

Palladium-Catalyzed Allenylation/6π-Electrocyclization and 1,3-Hydrogen Migration: an Access to Naphtho[1,2-b]furans

Chengyu Wang^*
, Yu Han
, Mengyuan Li
, Xuemei Zhou
, Lingkai Kong
, Yanzhong Li

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

Linyi University

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

6 Scopus citations

Abstract

A novel Pd-catalyzed method for the synthesis of various naphtho[1,2-b]furans from propargyl carboxylates bearing a furanyl group with organoborons is described. This cascade reaction involves Pd⁰-catalyzed allenylation, 6π-electrocyclization and 1,3-H migration process. Control experiments suggested the base (Cs₂CO₃) play an essential role for the hydrogen migration. Wide substrate scope with easily accessible starting materials and good functional group tolerance indicate that this protocol may provide a general approach to construct naphtho[1,2-b]furan frameworks which are important in natural product synthesis and medicinal chemistry.

Original language	English
Pages (from-to)	98-102
Number of pages	5
Journal	European Journal of Organic Chemistry
Volume	2020
Issue number	1
DOIs	https://doi.org/10.1002/ejoc.201901604
State	Published - 9 Jan 2020

Keywords

1,3-H shift
Alkenes
Electrocyclization
Naphtho[1,2-b]furan
Organic synthesis

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10.1002/ejoc.201901604

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title = "Palladium-Catalyzed Allenylation/6π-Electrocyclization and 1,3-Hydrogen Migration: an Access to Naphtho[1,2-b]furans",

abstract = "A novel Pd-catalyzed method for the synthesis of various naphtho[1,2-b]furans from propargyl carboxylates bearing a furanyl group with organoborons is described. This cascade reaction involves Pd0-catalyzed allenylation, 6π-electrocyclization and 1,3-H migration process. Control experiments suggested the base (Cs2CO3) play an essential role for the hydrogen migration. Wide substrate scope with easily accessible starting materials and good functional group tolerance indicate that this protocol may provide a general approach to construct naphtho[1,2-b]furan frameworks which are important in natural product synthesis and medicinal chemistry.",

keywords = "1,3-H shift, Alkenes, Electrocyclization, Naphtho[1,2-b]furan, Organic synthesis",

author = "Chengyu Wang and Yu Han and Mengyuan Li and Xuemei Zhou and Lingkai Kong and Yanzhong Li",

note = "Publisher Copyright: {\textcopyright} 2020 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2020",

month = jan,

day = "9",

doi = "10.1002/ejoc.201901604",

language = "英语",

volume = "2020",

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journal = "European Journal of Organic Chemistry",

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T1 - Palladium-Catalyzed Allenylation/6π-Electrocyclization and 1,3-Hydrogen Migration

T2 - an Access to Naphtho[1,2-b]furans

AU - Wang, Chengyu

AU - Han, Yu

AU - Li, Mengyuan

AU - Zhou, Xuemei

AU - Kong, Lingkai

AU - Li, Yanzhong

PY - 2020/1/9

Y1 - 2020/1/9

N2 - A novel Pd-catalyzed method for the synthesis of various naphtho[1,2-b]furans from propargyl carboxylates bearing a furanyl group with organoborons is described. This cascade reaction involves Pd0-catalyzed allenylation, 6π-electrocyclization and 1,3-H migration process. Control experiments suggested the base (Cs2CO3) play an essential role for the hydrogen migration. Wide substrate scope with easily accessible starting materials and good functional group tolerance indicate that this protocol may provide a general approach to construct naphtho[1,2-b]furan frameworks which are important in natural product synthesis and medicinal chemistry.

AB - A novel Pd-catalyzed method for the synthesis of various naphtho[1,2-b]furans from propargyl carboxylates bearing a furanyl group with organoborons is described. This cascade reaction involves Pd0-catalyzed allenylation, 6π-electrocyclization and 1,3-H migration process. Control experiments suggested the base (Cs2CO3) play an essential role for the hydrogen migration. Wide substrate scope with easily accessible starting materials and good functional group tolerance indicate that this protocol may provide a general approach to construct naphtho[1,2-b]furan frameworks which are important in natural product synthesis and medicinal chemistry.

KW - 1,3-H shift

KW - Alkenes

KW - Electrocyclization

KW - Naphtho[1,2-b]furan

KW - Organic synthesis

UR - https://www.scopus.com/pages/publications/85077078615

U2 - 10.1002/ejoc.201901604

DO - 10.1002/ejoc.201901604

M3 - 文章

AN - SCOPUS:85077078615

SN - 1434-193X

VL - 2020

SP - 98

EP - 102

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 1

ER -

Palladium-Catalyzed Allenylation/6π-Electrocyclization and 1,3-Hydrogen Migration: an Access to Naphtho[1,2-b]furans

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Keywords

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