Catalyst-free photocyclopropanation of dibromomalonates with alkenes: An approach to multisubstituted cyclopropanes

Yanbin Zhang; Yong An; Jing Sun; Aishun Ding; Yu Wang; Ramon Rios; Hao Guo

doi:10.1016/j.tetlet.2015.10.012

Catalyst-free photocyclopropanation of dibromomalonates with alkenes: An approach to multisubstituted cyclopropanes

Yanbin Zhang
, Yong An
, Jing Sun
, Aishun Ding
, Yu Wang
, Ramon Rios
, Hao Guo

Chemistry

Fudan University
Fudan University Shanghai Cancer Center
Shanghai Institute of Organic Chemistry Chinese Academy of Sciences

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

7 Scopus citations

Abstract

We report herein a novel photocyclopropanation of dibromomalonates with alkenes in the presence of Hünig base. This protocol provides an environmentally benign approach for the synthesis of multisubstituted cyclopropanes, since no catalyst is required. The Photo-induced Electron Transfer (PET) from Hünig base to dibromomalonate is the key process during this transformation.

Original language	British English
Pages (from-to)	6499-6502
Number of pages	4
Journal	Tetrahedron Letters
Volume	56
Issue number	46
DOIs	https://doi.org/10.1016/j.tetlet.2015.10.012
State	Published - 18 Nov 2015

Keywords

Catalyst-free
Cyclopropanation
Cyclopropane
Mechanism
Photochemistry

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10.1016/j.tetlet.2015.10.012

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title = "Catalyst-free photocyclopropanation of dibromomalonates with alkenes: An approach to multisubstituted cyclopropanes",

abstract = "We report herein a novel photocyclopropanation of dibromomalonates with alkenes in the presence of H{\"u}nig base. This protocol provides an environmentally benign approach for the synthesis of multisubstituted cyclopropanes, since no catalyst is required. The Photo-induced Electron Transfer (PET) from H{\"u}nig base to dibromomalonate is the key process during this transformation.",

keywords = "Catalyst-free, Cyclopropanation, Cyclopropane, Mechanism, Photochemistry",

author = "Yanbin Zhang and Yong An and Jing Sun and Aishun Ding and Yu Wang and Ramon Rios and Hao Guo",

note = "Funding Information: We greatly acknowledge the financial support from National Basic Research Program of China (973 Program, 2012CB720300 ), International Science \& Technology Cooperation Program of China ( 2014DFE40130 ), Shanghai Rising-Star Program ( 14QA1400500 ), and Science and Technology Commission of Shanghai Municipality ( 14ZR1407300 ). Publisher Copyright: {\textcopyright} 2015 Elsevier Ltd. All rights reserved.",

year = "2015",

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doi = "10.1016/j.tetlet.2015.10.012",

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T1 - Catalyst-free photocyclopropanation of dibromomalonates with alkenes

T2 - An approach to multisubstituted cyclopropanes

AU - Zhang, Yanbin

AU - An, Yong

AU - Sun, Jing

AU - Ding, Aishun

AU - Wang, Yu

AU - Rios, Ramon

AU - Guo, Hao

N1 - Funding Information: We greatly acknowledge the financial support from National Basic Research Program of China (973 Program, 2012CB720300 ), International Science & Technology Cooperation Program of China ( 2014DFE40130 ), Shanghai Rising-Star Program ( 14QA1400500 ), and Science and Technology Commission of Shanghai Municipality ( 14ZR1407300 ). Publisher Copyright: © 2015 Elsevier Ltd. All rights reserved.

PY - 2015/11/18

Y1 - 2015/11/18

N2 - We report herein a novel photocyclopropanation of dibromomalonates with alkenes in the presence of Hünig base. This protocol provides an environmentally benign approach for the synthesis of multisubstituted cyclopropanes, since no catalyst is required. The Photo-induced Electron Transfer (PET) from Hünig base to dibromomalonate is the key process during this transformation.

AB - We report herein a novel photocyclopropanation of dibromomalonates with alkenes in the presence of Hünig base. This protocol provides an environmentally benign approach for the synthesis of multisubstituted cyclopropanes, since no catalyst is required. The Photo-induced Electron Transfer (PET) from Hünig base to dibromomalonate is the key process during this transformation.

KW - Catalyst-free

KW - Cyclopropanation

KW - Cyclopropane

KW - Mechanism

KW - Photochemistry

UR - https://www.scopus.com/pages/publications/84946147319

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DO - 10.1016/j.tetlet.2015.10.012

M3 - Article

AN - SCOPUS:84946147319

SN - 0040-4039

VL - 56

SP - 6499

EP - 6502

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 46

ER -

Catalyst-free photocyclopropanation of dibromomalonates with alkenes: An approach to multisubstituted cyclopropanes

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