Catalytic Double [2 + 2] Cycloaddition Relay Enabled C-C Triple Bond Cleavage of Yne-Allenones

Heng Li; Wen Juan Hao; Mian Wang; Xue Qin; Shu Jiang Tu; Peng Zhou; Guigen Li; Jianyi Wang; Bo Jiang

doi:10.1021/acs.orglett.8b01841

Catalytic Double [2 + 2] Cycloaddition Relay Enabled C-C Triple Bond Cleavage of Yne-Allenones

Heng Li, Wen Juan Hao, Mian Wang, Xue Qin, Shu Jiang Tu, Peng Zhou, Guigen Li, Jianyi Wang, Bo Jiang

Chemistry and Biochemistry

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

24 Scopus citations

Abstract

An unusual catalytic double [2 + 2] cycloaddition relay reaction of yne-allenones with unactivated alkenes and alkynes has been achieved, which enabled C-C triple-bond cleavage to access more than 60 examples of functionalized phenanthren-9-ols with generally good yields. This reaction provides a regioselective and practical method for the construction of carbocyclic ring systems with a high degree of functional group compatibility. Aside from surveying the scope of this transformation, mechanistic details of this process are provided by conducting systematic theoretical calculations.

Original language	English
Pages (from-to)	4362-4366
Number of pages	5
Journal	Organic Letters
Volume	20
Issue number	14
DOIs	https://doi.org/10.1021/acs.orglett.8b01841
State	Published - Jul 20 2018

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title = "Catalytic Double [2 + 2] Cycloaddition Relay Enabled C-C Triple Bond Cleavage of Yne-Allenones",

abstract = "An unusual catalytic double [2 + 2] cycloaddition relay reaction of yne-allenones with unactivated alkenes and alkynes has been achieved, which enabled C-C triple-bond cleavage to access more than 60 examples of functionalized phenanthren-9-ols with generally good yields. This reaction provides a regioselective and practical method for the construction of carbocyclic ring systems with a high degree of functional group compatibility. Aside from surveying the scope of this transformation, mechanistic details of this process are provided by conducting systematic theoretical calculations.",

author = "Heng Li and Hao, {Wen Juan} and Mian Wang and Xue Qin and Tu, {Shu Jiang} and Peng Zhou and Guigen Li and Jianyi Wang and Bo Jiang",

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T1 - Catalytic Double [2 + 2] Cycloaddition Relay Enabled C-C Triple Bond Cleavage of Yne-Allenones

AU - Li, Heng

AU - Hao, Wen Juan

AU - Wang, Mian

AU - Qin, Xue

AU - Tu, Shu Jiang

AU - Zhou, Peng

AU - Li, Guigen

AU - Wang, Jianyi

AU - Jiang, Bo

PY - 2018/7/20

Y1 - 2018/7/20

N2 - An unusual catalytic double [2 + 2] cycloaddition relay reaction of yne-allenones with unactivated alkenes and alkynes has been achieved, which enabled C-C triple-bond cleavage to access more than 60 examples of functionalized phenanthren-9-ols with generally good yields. This reaction provides a regioselective and practical method for the construction of carbocyclic ring systems with a high degree of functional group compatibility. Aside from surveying the scope of this transformation, mechanistic details of this process are provided by conducting systematic theoretical calculations.

AB - An unusual catalytic double [2 + 2] cycloaddition relay reaction of yne-allenones with unactivated alkenes and alkynes has been achieved, which enabled C-C triple-bond cleavage to access more than 60 examples of functionalized phenanthren-9-ols with generally good yields. This reaction provides a regioselective and practical method for the construction of carbocyclic ring systems with a high degree of functional group compatibility. Aside from surveying the scope of this transformation, mechanistic details of this process are provided by conducting systematic theoretical calculations.

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JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

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