Site selectivity;
bmlm]OH;
Green protocol;
C-C bond functionalization;
Ambient conditions;
BASIC IONIC LIQUID;
ACTIVE METHYLENE-COMPOUNDS;
MICHAEL ADDITION;
EFFICIENT PROTOCOL;
CARBONYL-COMPOUNDS;
MATERIALS SCIENCE;
N-HETEROCYCLES;
CHEMISTRY;
DERIVATIVES;
SOLVENT;
D O I:
10.1016/j.tetlet.2018.01.010
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
Effective methodology that activates selectively either end of a carbon-carbon triple bond requires key challenge of differentiating between the multitude of C-C bonds present in complex organic molecule. The synthetic strategy exploited the electronic biases within the substrate and successfully achieved site-selective [bmIm]OH catalyzed C-C bond functionalization under mild reaction conditions. This resulted in C-2-selective addition of phenacyl bromide on p-substituted phenyl acetylene and C-1 selective addition on the o-substituted phenyl acetylene leading to C-C bond formation. The reaction proceeded smoothly with excellent yield under ambient conditions. This report demonstrates the progress on the catalytic activity of recyclable EbrnImIOH for selective C-C bond formation. (C) 2018 Elsevier Ltd. All rights reserved.
机构:
Peking Univ, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R ChinaPeking Univ, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
Liu, Jianzhong
Pan, Jun
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机构:
Peking Univ, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R ChinaPeking Univ, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
Pan, Jun
Luo, Xiao
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机构:
Peking Univ, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R ChinaPeking Univ, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
Luo, Xiao
Qiu, Xu
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机构:
Peking Univ, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R ChinaPeking Univ, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
Qiu, Xu
Zhang, Cheng
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机构:
Peking Univ, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R ChinaPeking Univ, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
Zhang, Cheng
Jiao, Ning
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机构:
Peking Univ, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
Chinese Acad Sci, State Key Lab Organomet Chem, Shanghai 200032, Peoples R ChinaPeking Univ, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
机构:
Univ Massachusetts Amherst, Chem Engn Dept, Amherst, MA 01003 USA
Chinese Acad Sci, Guangzhou Inst Energy Convers, Guangdong Prov Key Lab New & Renewable Energy Res, CAS Key Lab Renewable Energy, Guangzhou 510640, Peoples R China
Univ Chinese Acad Sci, Beijing 100049, Peoples R ChinaSoutheast Univ, Sch Energy & Environm, Key Lab Energy Thermal Convers & Control, Minist Educ, Nanjing 210096, Peoples R China
Hu, Yuzhen
Cui, Yanbin
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机构:
Chinese Acad Sci, Guangzhou Inst Energy Convers, Guangdong Prov Key Lab New & Renewable Energy Res, CAS Key Lab Renewable Energy, Guangzhou 510640, Peoples R ChinaSoutheast Univ, Sch Energy & Environm, Key Lab Energy Thermal Convers & Control, Minist Educ, Nanjing 210096, Peoples R China
Cui, Yanbin
Zhao, Shuoxiao
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机构:
Chinese Acad Sci, Guangzhou Inst Energy Convers, Guangdong Prov Key Lab New & Renewable Energy Res, CAS Key Lab Renewable Energy, Guangzhou 510640, Peoples R ChinaSoutheast Univ, Sch Energy & Environm, Key Lab Energy Thermal Convers & Control, Minist Educ, Nanjing 210096, Peoples R China
Zhao, Shuoxiao
Zhao, Xuelai
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h-index: 0
机构:
Chinese Acad Sci, Guangzhou Inst Energy Convers, Guangdong Prov Key Lab New & Renewable Energy Res, CAS Key Lab Renewable Energy, Guangzhou 510640, Peoples R ChinaSoutheast Univ, Sch Energy & Environm, Key Lab Energy Thermal Convers & Control, Minist Educ, Nanjing 210096, Peoples R China
Zhao, Xuelai
Hu, Xiaohong
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h-index: 0
机构:
Southeast Univ, Sch Energy & Environm, Key Lab Energy Thermal Convers & Control, Minist Educ, Nanjing 210096, Peoples R ChinaSoutheast Univ, Sch Energy & Environm, Key Lab Energy Thermal Convers & Control, Minist Educ, Nanjing 210096, Peoples R China
Hu, Xiaohong
Song, Zhenlong
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h-index: 0
机构:
Chinese Acad Sci, Guangzhou Inst Energy Convers, Guangdong Prov Key Lab New & Renewable Energy Res, CAS Key Lab Renewable Energy, Guangzhou 510640, Peoples R ChinaSoutheast Univ, Sch Energy & Environm, Key Lab Energy Thermal Convers & Control, Minist Educ, Nanjing 210096, Peoples R China
Song, Zhenlong
Fan, Wei
论文数: 0引用数: 0
h-index: 0
机构:
Univ Massachusetts Amherst, Chem Engn Dept, Amherst, MA 01003 USASoutheast Univ, Sch Energy & Environm, Key Lab Energy Thermal Convers & Control, Minist Educ, Nanjing 210096, Peoples R China
Fan, Wei
Zhang, Qi
论文数: 0引用数: 0
h-index: 0
机构:
Southeast Univ, Sch Energy & Environm, Key Lab Energy Thermal Convers & Control, Minist Educ, Nanjing 210096, Peoples R ChinaSoutheast Univ, Sch Energy & Environm, Key Lab Energy Thermal Convers & Control, Minist Educ, Nanjing 210096, Peoples R China