共 54 条
Rh(III)-Catalyzed meta-C-H Alkenylation with Alkynes
被引:81
作者:

Xu, Hua-Jin
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Nanjing Univ, Collaborat Innovat Ctr Adv Microstruct, Coordinat Chem Inst,Nanjing Natl Lab Microstruct, State Key Lab Coordinat Chem,Sch Chem & Chem Engn, Nanjing 210023, Jiangsu, Peoples R China Nanjing Univ, Collaborat Innovat Ctr Adv Microstruct, Coordinat Chem Inst,Nanjing Natl Lab Microstruct, State Key Lab Coordinat Chem,Sch Chem & Chem Engn, Nanjing 210023, Jiangsu, Peoples R China

Kang, Yan-Shang
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Nanjing Univ, Collaborat Innovat Ctr Adv Microstruct, Coordinat Chem Inst,Nanjing Natl Lab Microstruct, State Key Lab Coordinat Chem,Sch Chem & Chem Engn, Nanjing 210023, Jiangsu, Peoples R China Nanjing Univ, Collaborat Innovat Ctr Adv Microstruct, Coordinat Chem Inst,Nanjing Natl Lab Microstruct, State Key Lab Coordinat Chem,Sch Chem & Chem Engn, Nanjing 210023, Jiangsu, Peoples R China

Shi, Hang
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Scripps Res Inst, Dept Chem, 10550 N Torrey Pines Rd, La Jolla, CA 92037 USA Nanjing Univ, Collaborat Innovat Ctr Adv Microstruct, Coordinat Chem Inst,Nanjing Natl Lab Microstruct, State Key Lab Coordinat Chem,Sch Chem & Chem Engn, Nanjing 210023, Jiangsu, Peoples R China

Zhang, Ping
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Nanjing Univ, Collaborat Innovat Ctr Adv Microstruct, Coordinat Chem Inst,Nanjing Natl Lab Microstruct, State Key Lab Coordinat Chem,Sch Chem & Chem Engn, Nanjing 210023, Jiangsu, Peoples R China Nanjing Univ, Collaborat Innovat Ctr Adv Microstruct, Coordinat Chem Inst,Nanjing Natl Lab Microstruct, State Key Lab Coordinat Chem,Sch Chem & Chem Engn, Nanjing 210023, Jiangsu, Peoples R China

Chen, You-Ke
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Nanjing Univ, Collaborat Innovat Ctr Adv Microstruct, Coordinat Chem Inst,Nanjing Natl Lab Microstruct, State Key Lab Coordinat Chem,Sch Chem & Chem Engn, Nanjing 210023, Jiangsu, Peoples R China Nanjing Univ, Collaborat Innovat Ctr Adv Microstruct, Coordinat Chem Inst,Nanjing Natl Lab Microstruct, State Key Lab Coordinat Chem,Sch Chem & Chem Engn, Nanjing 210023, Jiangsu, Peoples R China

Zhang, Bing
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Nanjing Univ, Collaborat Innovat Ctr Adv Microstruct, Coordinat Chem Inst,Nanjing Natl Lab Microstruct, State Key Lab Coordinat Chem,Sch Chem & Chem Engn, Nanjing 210023, Jiangsu, Peoples R China Nanjing Univ, Collaborat Innovat Ctr Adv Microstruct, Coordinat Chem Inst,Nanjing Natl Lab Microstruct, State Key Lab Coordinat Chem,Sch Chem & Chem Engn, Nanjing 210023, Jiangsu, Peoples R China

Liu, Zhi-Qiang
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Nanjing Univ, Collaborat Innovat Ctr Adv Microstruct, Coordinat Chem Inst,Nanjing Natl Lab Microstruct, State Key Lab Coordinat Chem,Sch Chem & Chem Engn, Nanjing 210023, Jiangsu, Peoples R China Nanjing Univ, Collaborat Innovat Ctr Adv Microstruct, Coordinat Chem Inst,Nanjing Natl Lab Microstruct, State Key Lab Coordinat Chem,Sch Chem & Chem Engn, Nanjing 210023, Jiangsu, Peoples R China

Zhao, Jing
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Nanjing Univ, Collaborat Innovat Ctr Adv Microstruct, Coordinat Chem Inst,Nanjing Natl Lab Microstruct, State Key Lab Coordinat Chem,Sch Chem & Chem Engn, Nanjing 210023, Jiangsu, Peoples R China Nanjing Univ, Collaborat Innovat Ctr Adv Microstruct, Coordinat Chem Inst,Nanjing Natl Lab Microstruct, State Key Lab Coordinat Chem,Sch Chem & Chem Engn, Nanjing 210023, Jiangsu, Peoples R China

Sun, Wei-Yin
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Nanjing Univ, Collaborat Innovat Ctr Adv Microstruct, Coordinat Chem Inst,Nanjing Natl Lab Microstruct, State Key Lab Coordinat Chem,Sch Chem & Chem Engn, Nanjing 210023, Jiangsu, Peoples R China Nanjing Univ, Collaborat Innovat Ctr Adv Microstruct, Coordinat Chem Inst,Nanjing Natl Lab Microstruct, State Key Lab Coordinat Chem,Sch Chem & Chem Engn, Nanjing 210023, Jiangsu, Peoples R China

Yu, Jin-Quan
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机构:
Scripps Res Inst, Dept Chem, 10550 N Torrey Pines Rd, La Jolla, CA 92037 USA Nanjing Univ, Collaborat Innovat Ctr Adv Microstruct, Coordinat Chem Inst,Nanjing Natl Lab Microstruct, State Key Lab Coordinat Chem,Sch Chem & Chem Engn, Nanjing 210023, Jiangsu, Peoples R China

Lu, Yi
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机构:
Nanjing Univ, Collaborat Innovat Ctr Adv Microstruct, Coordinat Chem Inst,Nanjing Natl Lab Microstruct, State Key Lab Coordinat Chem,Sch Chem & Chem Engn, Nanjing 210023, Jiangsu, Peoples R China Nanjing Univ, Collaborat Innovat Ctr Adv Microstruct, Coordinat Chem Inst,Nanjing Natl Lab Microstruct, State Key Lab Coordinat Chem,Sch Chem & Chem Engn, Nanjing 210023, Jiangsu, Peoples R China
机构:
[1] Nanjing Univ, Collaborat Innovat Ctr Adv Microstruct, Coordinat Chem Inst,Nanjing Natl Lab Microstruct, State Key Lab Coordinat Chem,Sch Chem & Chem Engn, Nanjing 210023, Jiangsu, Peoples R China
[2] Scripps Res Inst, Dept Chem, 10550 N Torrey Pines Rd, La Jolla, CA 92037 USA
基金:
美国国家科学基金会;
中国国家自然科学基金;
关键词:
BOND FUNCTIONALIZATION;
DIRECTING GROUP;
ARYLATION;
OLEFINATION;
BORYLATION;
ALKYLATION;
LIGAND;
ACTIVATION;
ARENES;
CATALYSIS;
D O I:
10.1021/jacs.8b11038
中图分类号:
O6 [化学];
学科分类号:
0703 ;
摘要:
Rh(III)-catalyzed meta-C-H functionalization reactions are still rare. Herein, we report the first example of Rh(III)-catalyzed meta-C-H alkenylation with disubstituted alkynes directed by a U-shaped nitrile template. Exclusive regio-selectivity has been achieved using unsymmetrical aryl and alkyl-disubstituted alkynes to afford synthetically valuable trisubstituted olefins. Propargyl alcohols are also compatible, affording complex allylic alcohols. Notably, transition metal-catalyzed metaalkenylation with alkynes has not been successful with Pd catalysts.
引用
收藏
页码:76 / 79
页数:4
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共 54 条
[21]
Meta-Selective C-H Functionalization Using a Nitrile-Based Directing Group and Cleavable Si-Tether
[J].
Lee, Sunggi
;
Lee, Hyelee
;
Tan, Kian L.
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2013, 135 (50)
:18778-18781

Lee, Sunggi
论文数: 0 引用数: 0
h-index: 0
机构:
Boston Coll, Chestnut Hill, MA 02467 USA Boston Coll, Chestnut Hill, MA 02467 USA

Lee, Hyelee
论文数: 0 引用数: 0
h-index: 0
机构:
Boston Coll, Chestnut Hill, MA 02467 USA Boston Coll, Chestnut Hill, MA 02467 USA

Tan, Kian L.
论文数: 0 引用数: 0
h-index: 0
机构:
Boston Coll, Chestnut Hill, MA 02467 USA Boston Coll, Chestnut Hill, MA 02467 USA
[22]
Activation of remote meta-C-H bonds assisted by an end-on template
[J].
Leow, Dasheng
;
Li, Gang
;
Mei, Tian-Sheng
;
Yu, Jin-Quan
.
NATURE,
2012, 486 (7404)
:518-522

Leow, Dasheng
论文数: 0 引用数: 0
h-index: 0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

Li, Gang
论文数: 0 引用数: 0
h-index: 0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

Mei, Tian-Sheng
论文数: 0 引用数: 0
h-index: 0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

Yu, Jin-Quan
论文数: 0 引用数: 0
h-index: 0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
[23]
N-Acyl Amino Acid Ligands for Ruthenium(II)-Catalyzed meta-C-H tert-Alkylation with Removable Auxiliaries
[J].
Li, Jie
;
Warratz, Svenja
;
Zell, Daniel
;
De Sarkar, Suman
;
Ishikawa, Eloisa Eriko
;
Ackermann, Lutz
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2015, 137 (43)
:13894-13901

Li, Jie
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany

Warratz, Svenja
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany

Zell, Daniel
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany

De Sarkar, Suman
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany

Ishikawa, Eloisa Eriko
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany

Ackermann, Lutz
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
[24]
Pd(II)-catalyzed remote regiodivergent ortho- and meta-C-H functionalizations of phenylethylamines
[J].
Li, Shangda
;
Ji, Huafang
;
Cai, Lei
;
Li, Gang
.
CHEMICAL SCIENCE,
2015, 6 (10)
:5595-5600

Li, Shangda
论文数: 0 引用数: 0
h-index: 0
机构:
Chinese Acad Sci, Fujian Inst Res Struct Matter, Key Lab Coal Ethylene Glycol & Its Related Techno, Fuzhou 350002, Fujian, Peoples R China Chinese Acad Sci, Fujian Inst Res Struct Matter, Key Lab Coal Ethylene Glycol & Its Related Techno, Fuzhou 350002, Fujian, Peoples R China

Ji, Huafang
论文数: 0 引用数: 0
h-index: 0
机构:
Chinese Acad Sci, Fujian Inst Res Struct Matter, Key Lab Coal Ethylene Glycol & Its Related Techno, Fuzhou 350002, Fujian, Peoples R China Chinese Acad Sci, Fujian Inst Res Struct Matter, Key Lab Coal Ethylene Glycol & Its Related Techno, Fuzhou 350002, Fujian, Peoples R China

Cai, Lei
论文数: 0 引用数: 0
h-index: 0
机构:
Chinese Acad Sci, Fujian Inst Res Struct Matter, Key Lab Coal Ethylene Glycol & Its Related Techno, Fuzhou 350002, Fujian, Peoples R China Chinese Acad Sci, Fujian Inst Res Struct Matter, Key Lab Coal Ethylene Glycol & Its Related Techno, Fuzhou 350002, Fujian, Peoples R China

Li, Gang
论文数: 0 引用数: 0
h-index: 0
机构:
Chinese Acad Sci, Fujian Inst Res Struct Matter, Key Lab Coal Ethylene Glycol & Its Related Techno, Fuzhou 350002, Fujian, Peoples R China
Chinese Acad Sci, State Key Lab Struct Chem, Fuzhou 350002, Fujian, Peoples R China Chinese Acad Sci, Fujian Inst Res Struct Matter, Key Lab Coal Ethylene Glycol & Its Related Techno, Fuzhou 350002, Fujian, Peoples R China
[25]
Overriding Ortho-Para Selectivity via a Traceless Directing Group Relay Strategy: The Meta-Selective Arylation of Phenols
[J].
Luo, Junfei
;
Preciado, Sara
;
Larrosa, Igor
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2014, 136 (11)
:4109-4112

Luo, Junfei
论文数: 0 引用数: 0
h-index: 0
机构:
Queen Mary Univ London, Sch Biol & Chem Sci, London E1 4NS, England Queen Mary Univ London, Sch Biol & Chem Sci, London E1 4NS, England

Preciado, Sara
论文数: 0 引用数: 0
h-index: 0
机构:
Queen Mary Univ London, Sch Biol & Chem Sci, London E1 4NS, England Queen Mary Univ London, Sch Biol & Chem Sci, London E1 4NS, England

Larrosa, Igor
论文数: 0 引用数: 0
h-index: 0
机构:
Queen Mary Univ London, Sch Biol & Chem Sci, London E1 4NS, England Queen Mary Univ London, Sch Biol & Chem Sci, London E1 4NS, England
[26]
Palladium-Catalyzed Ligand-Directed C-H Functionalization Reactions
[J].
Lyons, Thomas W.
;
Sanford, Melanie S.
.
CHEMICAL REVIEWS,
2010, 110 (02)
:1147-1169

Lyons, Thomas W.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

Sanford, Melanie S.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA
[27]
RhI/RhIII catalyst-controlled divergent aryl/heteroaryl C-H bond functionalization of picolinamides with alkynes
[J].
Manu Martinez, Angel
;
Echavarren, Javier
;
Alonso, Ines
;
Rodriguez, Nuria
;
Gomez Arrayas, Ramon
;
Carretero, Juan C.
.
CHEMICAL SCIENCE,
2015, 6 (10)
:5802-5814

Manu Martinez, Angel
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Autonoma Madrid, E-28049 Madrid, Spain Univ Autonoma Madrid, E-28049 Madrid, Spain

Echavarren, Javier
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Autonoma Madrid, E-28049 Madrid, Spain Univ Autonoma Madrid, E-28049 Madrid, Spain

Alonso, Ines
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Autonoma Madrid, E-28049 Madrid, Spain Univ Autonoma Madrid, E-28049 Madrid, Spain

Rodriguez, Nuria
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Autonoma Madrid, E-28049 Madrid, Spain Univ Autonoma Madrid, E-28049 Madrid, Spain

Gomez Arrayas, Ramon
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Autonoma Madrid, E-28049 Madrid, Spain Univ Autonoma Madrid, E-28049 Madrid, Spain

Carretero, Juan C.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Autonoma Madrid, E-28049 Madrid, Spain Univ Autonoma Madrid, E-28049 Madrid, Spain
[28]
Directed ortho-meta'- and meta-meta'-dimetalations: A template base approach to deprotonation
[J].
Martinez-Martinez, Antonio J.
;
Kennedy, Alan R.
;
Mulvey, Robert E.
;
O'Hara, Charles T.
.
SCIENCE,
2014, 346 (6211)
:834-837

Martinez-Martinez, Antonio J.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Strathclyde, Dept Pure & Appl Chem, WestCHEM, Glasgow G1 1XL, Lanark, Scotland Univ Strathclyde, Dept Pure & Appl Chem, WestCHEM, Glasgow G1 1XL, Lanark, Scotland

Kennedy, Alan R.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Strathclyde, Dept Pure & Appl Chem, WestCHEM, Glasgow G1 1XL, Lanark, Scotland Univ Strathclyde, Dept Pure & Appl Chem, WestCHEM, Glasgow G1 1XL, Lanark, Scotland

Mulvey, Robert E.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Strathclyde, Dept Pure & Appl Chem, WestCHEM, Glasgow G1 1XL, Lanark, Scotland Univ Strathclyde, Dept Pure & Appl Chem, WestCHEM, Glasgow G1 1XL, Lanark, Scotland

O'Hara, Charles T.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Strathclyde, Dept Pure & Appl Chem, WestCHEM, Glasgow G1 1XL, Lanark, Scotland Univ Strathclyde, Dept Pure & Appl Chem, WestCHEM, Glasgow G1 1XL, Lanark, Scotland
[29]
Meta halogenation of 1,3-disubstituted arenes via iridium-catalyzed arene borylation
[J].
Murphy, Jaclyn M.
;
Liao, Xuebin
;
Hartwig, John F.
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2007, 129 (50)
:15434-+

Murphy, Jaclyn M.
论文数: 0 引用数: 0
h-index: 0
机构: Univ Illinois, Dept Chem, Urbana, IL 61801 USA

Liao, Xuebin
论文数: 0 引用数: 0
h-index: 0
机构: Univ Illinois, Dept Chem, Urbana, IL 61801 USA

Hartwig, John F.
论文数: 0 引用数: 0
h-index: 0
机构: Univ Illinois, Dept Chem, Urbana, IL 61801 USA
[30]
Rhodium(III)-Catalyzed Ortho-Alkenylation through C-H Bond Cleavage Directed by Sulfoxide Groups
[J].
Nobushige, Kazunori
;
Hirano, Koji
;
Satoh, Tetsuya
;
Miura, Masahiro
.
ORGANIC LETTERS,
2014, 16 (04)
:1188-1191

Nobushige, Kazunori
论文数: 0 引用数: 0
h-index: 0
机构:
Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan

Hirano, Koji
论文数: 0 引用数: 0
h-index: 0
机构:
Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan

Satoh, Tetsuya
论文数: 0 引用数: 0
h-index: 0
机构:
Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
JST, ACT C, Kawaguchi, Saitama 3320012, Japan Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan

Miura, Masahiro
论文数: 0 引用数: 0
h-index: 0
机构:
Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan