共 34 条
Rhodium(III)-catalyzed C-H functionalization of C-alkenyl azoles with sulfoxonium ylides for the synthesis of bridgehead N-fused [5,6]-bicyclic heterocycles
被引:38
作者:

Hoang, Gia L.
论文数: 0 引用数: 0
h-index: 0
机构:
Yale Univ, Dept Chem, New Haven, CT 06520 USA Yale Univ, Dept Chem, New Haven, CT 06520 USA

Ellman, Jonathan A.
论文数: 0 引用数: 0
h-index: 0
机构:
Yale Univ, Dept Chem, New Haven, CT 06520 USA Yale Univ, Dept Chem, New Haven, CT 06520 USA
机构:
[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA
来源:
关键词:
C-H functionalization;
Rhodium;
Sulfoxonium ylide;
Catalysis;
Nitrogen heterocycle;
BOND FUNCTIONALIZATIONS;
DIAZO-COMPOUNDS;
ALKYNES;
ACTIVATION;
ANNULATIONS;
INSERTION;
RHODIUM;
PHARMACEUTICALS;
CLEAVAGE;
D O I:
10.1016/j.tet.2018.03.062
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
The synthesis of bridgehead N-fused [5,6]-bicyclic heterocycles via rhodium(III)-catalyzed C-H functionalization of C-alkenyl azoles with sulfoxonium ylides is disclosed. Reactions proceeded in good to high yields for a range of aryl, heteroaryl and alkyl sulfoxonium ylides. In addition, 2-alkenyl imidazoles with different substitution patterns as well as C-alkenyl triazoles were effective inputs. The reaction could also be performed under straightforward bench top conditions. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3318 / 3324
页数:7
相关论文
共 34 条
[21]
Rhodium(III)-Catalyzed Nonaromatic sp2 C-H Activation/Annulation Using NHC as a Directing and Functionalizable Group
[J].
Thenarukandiyil, Ranjeesh
;
Thrikkykkal, Hridya
;
Choudhury, Joyanta
.
ORGANOMETALLICS,
2016, 35 (17)
:3007-3013

Thenarukandiyil, Ranjeesh
论文数: 0 引用数: 0
h-index: 0
机构:
Indian Inst Sci Educ & Res Bhopal, Dept Chem, Organometall & Smart Mat Lab, Bhopal 462066, India Indian Inst Sci Educ & Res Bhopal, Dept Chem, Organometall & Smart Mat Lab, Bhopal 462066, India

Thrikkykkal, Hridya
论文数: 0 引用数: 0
h-index: 0
机构:
Indian Inst Sci Educ & Res Bhopal, Dept Chem, Organometall & Smart Mat Lab, Bhopal 462066, India Indian Inst Sci Educ & Res Bhopal, Dept Chem, Organometall & Smart Mat Lab, Bhopal 462066, India

Choudhury, Joyanta
论文数: 0 引用数: 0
h-index: 0
机构:
Indian Inst Sci Educ & Res Bhopal, Dept Chem, Organometall & Smart Mat Lab, Bhopal 462066, India Indian Inst Sci Educ & Res Bhopal, Dept Chem, Organometall & Smart Mat Lab, Bhopal 462066, India
[22]
Fluorescent naphthyl- and anthrylazoles from the catalytic coupling of phenylazoles with internal alkynes through the cleavage of multiple, C-H bonds
[J].
Umeda, Nobuyoshi
;
Tsurugi, Hayato
;
Satoh, Tetsuya
;
Miura, Masahiro
.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2008, 47 (21)
:4019-4022

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

Tsurugi, Hayato
论文数: 0 引用数: 0
h-index: 0
机构:
Osaka Univ, Fac Engn, Dept Appl Chem, Osaka 5650871, Japan Osaka Univ, Fac Engn, Dept Appl Chem, 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, Osaka 5650871, Japan Osaka Univ, Fac Engn, Dept Appl Chem, 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, Osaka 5650871, Japan Osaka Univ, Fac Engn, Dept Appl Chem, Osaka 5650871, Japan
[23]
Analysis of the Structural Diversity, Substitution Patterns, and Frequency of Nitrogen Heterocycles among US FDA Approved Pharmaceuticals
[J].
Vitaku, Edon
;
Smith, David T.
;
Njardarson, Jon T.
.
JOURNAL OF MEDICINAL CHEMISTRY,
2014, 57 (24)
:10257-10274

Vitaku, Edon
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Arizona, Dept Chem & Biochem, Tucson, AZ 85721 USA Univ Arizona, Dept Chem & Biochem, Tucson, AZ 85721 USA

Smith, David T.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Arizona, Dept Chem & Biochem, Tucson, AZ 85721 USA Univ Arizona, Dept Chem & Biochem, Tucson, AZ 85721 USA

Njardarson, Jon T.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Arizona, Dept Chem & Biochem, Tucson, AZ 85721 USA Univ Arizona, Dept Chem & Biochem, Tucson, AZ 85721 USA
[24]
SYNTHESIS OF AN ANTI-alpha-AMINO EPOXIDE BY ONE-CARBON HOMOLOGATION OF AN alpha-AMINO ESTER: (2S, 3S)-1,2-EPOXY-3-(BOC-AMINO)-4-PHENYLBUTANE
[J].
Wang, Dengjin
;
Nugent, William A.
.
ORGANIC SYNTHESES,
2007, 84
:58-+

Wang, Dengjin
论文数: 0 引用数: 0
h-index: 0
机构:
DuPont Merck Pharmaceut, Dept Proc Res & Dev, Wilmington, DE 19880 USA DuPont Merck Pharmaceut, Dept Proc Res & Dev, Wilmington, DE 19880 USA

Nugent, William A.
论文数: 0 引用数: 0
h-index: 0
机构:
Bristol Myers Squibb Co, Proc Res & Dev Dept, Princeton, NJ 08543 USA DuPont Merck Pharmaceut, Dept Proc Res & Dev, Wilmington, DE 19880 USA
[25]
One-carbon chain extension of esters to α-chloroketones:: A safer route without diazomethane
[J].
Wang, DJ
;
Schwinden, MD
;
Radesca, L
;
Patel, B
;
Kronenthal, D
;
Huang, MH
;
Nugent, WA
.
JOURNAL OF ORGANIC CHEMISTRY,
2004, 69 (05)
:1629-1633

Wang, DJ
论文数: 0 引用数: 0
h-index: 0
机构:
Bristol Myers Squibb Co, Pharmaceut Res Inst, Proc Res & Dev Dept, Princeton, NJ 08543 USA Bristol Myers Squibb Co, Pharmaceut Res Inst, Proc Res & Dev Dept, Princeton, NJ 08543 USA

Schwinden, MD
论文数: 0 引用数: 0
h-index: 0
机构:
Bristol Myers Squibb Co, Pharmaceut Res Inst, Proc Res & Dev Dept, Princeton, NJ 08543 USA Bristol Myers Squibb Co, Pharmaceut Res Inst, Proc Res & Dev Dept, Princeton, NJ 08543 USA

Radesca, L
论文数: 0 引用数: 0
h-index: 0
机构:
Bristol Myers Squibb Co, Pharmaceut Res Inst, Proc Res & Dev Dept, Princeton, NJ 08543 USA Bristol Myers Squibb Co, Pharmaceut Res Inst, Proc Res & Dev Dept, Princeton, NJ 08543 USA

Patel, B
论文数: 0 引用数: 0
h-index: 0
机构:
Bristol Myers Squibb Co, Pharmaceut Res Inst, Proc Res & Dev Dept, Princeton, NJ 08543 USA Bristol Myers Squibb Co, Pharmaceut Res Inst, Proc Res & Dev Dept, Princeton, NJ 08543 USA

Kronenthal, D
论文数: 0 引用数: 0
h-index: 0
机构:
Bristol Myers Squibb Co, Pharmaceut Res Inst, Proc Res & Dev Dept, Princeton, NJ 08543 USA Bristol Myers Squibb Co, Pharmaceut Res Inst, Proc Res & Dev Dept, Princeton, NJ 08543 USA

Huang, MH
论文数: 0 引用数: 0
h-index: 0
机构:
Bristol Myers Squibb Co, Pharmaceut Res Inst, Proc Res & Dev Dept, Princeton, NJ 08543 USA Bristol Myers Squibb Co, Pharmaceut Res Inst, Proc Res & Dev Dept, Princeton, NJ 08543 USA

Nugent, WA
论文数: 0 引用数: 0
h-index: 0
机构:
Bristol Myers Squibb Co, Pharmaceut Res Inst, Proc Res & Dev Dept, Princeton, NJ 08543 USA Bristol Myers Squibb Co, Pharmaceut Res Inst, Proc Res & Dev Dept, Princeton, NJ 08543 USA
[26]
Ruthenium catalyzed oxidative annulation with alkynes via cascade C-H/N-H bond functionalizations
[J].
Wang, Rui
;
Falck, J. R.
.
JOURNAL OF ORGANOMETALLIC CHEMISTRY,
2014, 759
:33-36

Wang, Rui
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Texas SW Med Ctr Dallas, Dept Biochem, Div Chem, Dallas, TX 75390 USA Univ Texas SW Med Ctr Dallas, Dept Biochem, Div Chem, Dallas, TX 75390 USA

Falck, J. R.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Texas SW Med Ctr Dallas, Dept Biochem, Div Chem, Dallas, TX 75390 USA Univ Texas SW Med Ctr Dallas, Dept Biochem, Div Chem, Dallas, TX 75390 USA
[27]
Rh-Catalyzed Annulation of ortho-C-H Bonds of 2-Arylimidazoles with 1,4,2-Dioxazol-5-ones toward 5-Arylimidazo[1,2-c]quinazolines
[J].
Wu, Xiaopeng
;
Sun, Song
;
Xu, Shengbo
;
Cheng, Jiang
.
ADVANCED SYNTHESIS & CATALYSIS,
2018, 360 (06)
:1111-1115

Wu, Xiaopeng
论文数: 0 引用数: 0
h-index: 0
机构:
Changzhou Univ, Jiangsu Prov Key Lab Fine Petrochem Engn, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, Changzhou 213164, Peoples R China Changzhou Univ, Jiangsu Prov Key Lab Fine Petrochem Engn, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, Changzhou 213164, Peoples R China

Sun, Song
论文数: 0 引用数: 0
h-index: 0
机构:
Changzhou Univ, Jiangsu Prov Key Lab Fine Petrochem Engn, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, Changzhou 213164, Peoples R China Changzhou Univ, Jiangsu Prov Key Lab Fine Petrochem Engn, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, Changzhou 213164, Peoples R China

Xu, Shengbo
论文数: 0 引用数: 0
h-index: 0
机构:
Changzhou Univ, Jiangsu Prov Key Lab Fine Petrochem Engn, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, Changzhou 213164, Peoples R China Changzhou Univ, Jiangsu Prov Key Lab Fine Petrochem Engn, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, Changzhou 213164, Peoples R China

Cheng, Jiang
论文数: 0 引用数: 0
h-index: 0
机构:
Changzhou Univ, Jiangsu Prov Key Lab Fine Petrochem Engn, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, Changzhou 213164, Peoples R China Changzhou Univ, Jiangsu Prov Key Lab Fine Petrochem Engn, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, Changzhou 213164, Peoples R China
[28]
Transition-Metal-Catalyzed Cross-Couplings through Carbene Migratory Insertion
[J].
Xia, Ying
;
Qiu, Di
;
Wang, Jianbo
.
CHEMICAL REVIEWS,
2017, 117 (23)
:13810-13889

Xia, Ying
论文数: 0 引用数: 0
h-index: 0
机构:
Peking Univ, Coll Chem, Minist Educ, BNLMS,Key Lab Bioorgan Chem & Mol Engn, Beijing 100871, Peoples R China Peking Univ, Coll Chem, Minist Educ, BNLMS,Key Lab Bioorgan Chem & Mol Engn, Beijing 100871, Peoples R China

Qiu, Di
论文数: 0 引用数: 0
h-index: 0
机构:
Peking Univ, Coll Chem, Minist Educ, BNLMS,Key Lab Bioorgan Chem & Mol Engn, Beijing 100871, Peoples R China Peking Univ, Coll Chem, Minist Educ, BNLMS,Key Lab Bioorgan Chem & Mol Engn, Beijing 100871, Peoples R China

Wang, Jianbo
论文数: 0 引用数: 0
h-index: 0
机构:
Peking Univ, Coll Chem, Minist Educ, BNLMS,Key Lab Bioorgan Chem & Mol Engn, Beijing 100871, Peoples R China Peking Univ, Coll Chem, Minist Educ, BNLMS,Key Lab Bioorgan Chem & Mol Engn, Beijing 100871, Peoples R China
[29]
Rhodium(III)-catalyzed chemodivergent annulations between N-methoxybenzamides and sulfoxonium ylides via C-H activation
[J].
Xu, Youwei
;
Zheng, Guangfan
;
Yang, Xifa
;
Li, Xingwei
.
CHEMICAL COMMUNICATIONS,
2018, 54 (06)
:670-673

Xu, Youwei
论文数: 0 引用数: 0
h-index: 0
机构:
Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China
Univ Chinese Acad Sci, Beijing 100049, Peoples R China Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China

Zheng, Guangfan
论文数: 0 引用数: 0
h-index: 0
机构:
Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China

Yang, Xifa
论文数: 0 引用数: 0
h-index: 0
机构:
Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China
Univ Chinese Acad Sci, Beijing 100049, Peoples R China Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China

Li, Xingwei
论文数: 0 引用数: 0
h-index: 0
机构:
Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China
[30]
Sulfoxonium Ylides as a Carbene Precursor in Rh(III)-Catalyzed C-H Acylmethylation of Arenes
[J].
Xu, Youwei
;
Zhou, Xukai
;
Zheng, Guangfan
;
Li, Xingwei
.
ORGANIC LETTERS,
2017, 19 (19)
:5256-5259

Xu, Youwei
论文数: 0 引用数: 0
h-index: 0
机构:
Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
Univ Chinese Acad Sci, Beijing 100049, Peoples R China Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China

Zhou, Xukai
论文数: 0 引用数: 0
h-index: 0
机构:
Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
Univ Chinese Acad Sci, Beijing 100049, Peoples R China Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China

Zheng, Guangfan
论文数: 0 引用数: 0
h-index: 0
机构:
Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China

Li, Xingwei
论文数: 0 引用数: 0
h-index: 0
机构:
Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China