Cobalt-Catalyzed Chemoselective Transfer Hydrogenative Cyclization Cascade of Enone-Tethered Aldehydes

Shuang Shuang Ma; Biao Ling Jiang; Zheng Kun Yu; Suo Jiang Zhang; Bao Hua Xu

doi:10.1021/acs.orglett.1c00992

Cobalt-Catalyzed Chemoselective Transfer Hydrogenative Cyclization Cascade of Enone-Tethered Aldehydes

Shuang Shuang Ma, Biao Ling Jiang, Zheng Kun Yu, Suo Jiang Zhang, Bao Hua Xu^*

^*Corresponding author for this work

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

8 Citations (Scopus)

Abstract

The ligand-free Co-catalyzed chemoselective reductive cyclization cascade of enone-tethered aldehydes with i-PrOH as the environmentally benign hydrogen surrogate is developed by this study. Mechanistic studies disclosed that such a protocol is initiated by an ortho-enone-assisted Co(I)-catalyzed reduction of the aldehyde functionality with i-PrOH. Meanwhile, the selectivity from the Michael-Aldol cycloreduction cascade to the oxa-Michael cascade is feasible and readily adjusted by the addition of steric Lewis bases, such as TEMPO and DABCO, delivering substituted 1H-indenes and dihydroisobenzofurans, respectively.

Original language	English
Pages (from-to)	3873-3878
Number of pages	6
Journal	Organic Letters
Volume	23
Issue number	10
DOIs	https://doi.org/10.1021/acs.orglett.1c00992
Publication status	Published - 21 May 2021
Externally published	Yes

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title = "Cobalt-Catalyzed Chemoselective Transfer Hydrogenative Cyclization Cascade of Enone-Tethered Aldehydes",

abstract = "The ligand-free Co-catalyzed chemoselective reductive cyclization cascade of enone-tethered aldehydes with i-PrOH as the environmentally benign hydrogen surrogate is developed by this study. Mechanistic studies disclosed that such a protocol is initiated by an ortho-enone-assisted Co(I)-catalyzed reduction of the aldehyde functionality with i-PrOH. Meanwhile, the selectivity from the Michael-Aldol cycloreduction cascade to the oxa-Michael cascade is feasible and readily adjusted by the addition of steric Lewis bases, such as TEMPO and DABCO, delivering substituted 1H-indenes and dihydroisobenzofurans, respectively.",

author = "Ma, {Shuang Shuang} and Jiang, {Biao Ling} and Yu, {Zheng Kun} and Zhang, {Suo Jiang} and Xu, {Bao Hua}",

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T1 - Cobalt-Catalyzed Chemoselective Transfer Hydrogenative Cyclization Cascade of Enone-Tethered Aldehydes

AU - Ma, Shuang Shuang

AU - Jiang, Biao Ling

AU - Yu, Zheng Kun

AU - Zhang, Suo Jiang

AU - Xu, Bao Hua

N1 - Publisher Copyright: ©

PY - 2021/5/21

Y1 - 2021/5/21

N2 - The ligand-free Co-catalyzed chemoselective reductive cyclization cascade of enone-tethered aldehydes with i-PrOH as the environmentally benign hydrogen surrogate is developed by this study. Mechanistic studies disclosed that such a protocol is initiated by an ortho-enone-assisted Co(I)-catalyzed reduction of the aldehyde functionality with i-PrOH. Meanwhile, the selectivity from the Michael-Aldol cycloreduction cascade to the oxa-Michael cascade is feasible and readily adjusted by the addition of steric Lewis bases, such as TEMPO and DABCO, delivering substituted 1H-indenes and dihydroisobenzofurans, respectively.

AB - The ligand-free Co-catalyzed chemoselective reductive cyclization cascade of enone-tethered aldehydes with i-PrOH as the environmentally benign hydrogen surrogate is developed by this study. Mechanistic studies disclosed that such a protocol is initiated by an ortho-enone-assisted Co(I)-catalyzed reduction of the aldehyde functionality with i-PrOH. Meanwhile, the selectivity from the Michael-Aldol cycloreduction cascade to the oxa-Michael cascade is feasible and readily adjusted by the addition of steric Lewis bases, such as TEMPO and DABCO, delivering substituted 1H-indenes and dihydroisobenzofurans, respectively.

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U2 - 10.1021/acs.orglett.1c00992

DO - 10.1021/acs.orglett.1c00992

M3 - Article

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AN - SCOPUS:85106374750

SN - 1523-7060

VL - 23

SP - 3873

EP - 3878

JO - Organic Letters

JF - Organic Letters

IS - 10

ER -

Cobalt-Catalyzed Chemoselective Transfer Hydrogenative Cyclization Cascade of Enone-Tethered Aldehydes

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