共 58 条
Amide Effects in C-H Activation: Noncovalent Interactions with L-Shaped Ligand for meta Borylation of Aromatic Amides
被引:115
作者:

Bisht, Ranjana
论文数: 0 引用数: 0
h-index: 0
机构:
CBMR, Div Mol Synth & Drug Discovery, SGPGIMS Campus,Raebareli Rd, Lucknow 226014, Uttar Pradesh, India CBMR, Div Mol Synth & Drug Discovery, SGPGIMS Campus,Raebareli Rd, Lucknow 226014, Uttar Pradesh, India

Hoque, Md Emdadul
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h-index: 0
机构:
CBMR, Div Mol Synth & Drug Discovery, SGPGIMS Campus,Raebareli Rd, Lucknow 226014, Uttar Pradesh, India CBMR, Div Mol Synth & Drug Discovery, SGPGIMS Campus,Raebareli Rd, Lucknow 226014, Uttar Pradesh, India

Chattopadhyay, Buddhadeb
论文数: 0 引用数: 0
h-index: 0
机构:
CBMR, Div Mol Synth & Drug Discovery, SGPGIMS Campus,Raebareli Rd, Lucknow 226014, Uttar Pradesh, India CBMR, Div Mol Synth & Drug Discovery, SGPGIMS Campus,Raebareli Rd, Lucknow 226014, Uttar Pradesh, India
机构:
[1] CBMR, Div Mol Synth & Drug Discovery, SGPGIMS Campus,Raebareli Rd, Lucknow 226014, Uttar Pradesh, India
关键词:
amides;
C-H activation;
borylation;
iridium;
noncovalent interactions;
IRIDIUM-CATALYZED BORYLATION;
BOND FORMATION;
SELECTIVE BORYLATION;
PI INTERACTIONS;
FUNCTIONALIZATION;
ARENES;
QUINOLINES;
DISTORTION;
CHEMISTRY;
RESONANCE;
D O I:
10.1002/anie.201809929
中图分类号:
O6 [化学];
学科分类号:
0703 ;
摘要:
A new concept for the meta-selective borylation of aromatic amides is described. It has been demonstrated that while esters gave para borylations, amides lead to meta borylations. For achieving high meta selectivity, an L-shaped bifunctional ligand has been employed and engages in an O center dot center dot center dot K noncovalent interaction with the oxygen atom of the moderately distorted amide carbonyl group. This interaction provides exceptional control for meta C-H activation/borylation.
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收藏
页码:15762 / 15766
页数:5
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共 58 条
- [1] Conquering amide planarity: Structural distortion and its hidden reactivity[J]. TETRAHEDRON LETTERS, 2018, 59 (13) : 1147 - 1158Adachi, Shinya论文数: 0 引用数: 0 h-index: 0机构: Inst Microbial Chem BIKAKEN, Shinagawa Ku, 3-14-23 Kamiosaki, Tokyo 1410021, Japan Inst Microbial Chem BIKAKEN, Shinagawa Ku, 3-14-23 Kamiosaki, Tokyo 1410021, JapanKumagai, Naoya论文数: 0 引用数: 0 h-index: 0机构: Inst Microbial Chem BIKAKEN, Shinagawa Ku, 3-14-23 Kamiosaki, Tokyo 1410021, Japan Inst Microbial Chem BIKAKEN, Shinagawa Ku, 3-14-23 Kamiosaki, Tokyo 1410021, JapanShibasaki, Masakatsu论文数: 0 引用数: 0 h-index: 0机构: Inst Microbial Chem BIKAKEN, Shinagawa Ku, 3-14-23 Kamiosaki, Tokyo 1410021, Japan Inst Microbial Chem BIKAKEN, Shinagawa Ku, 3-14-23 Kamiosaki, Tokyo 1410021, Japan
- [2] RELATIONSHIP BETWEEN AMIDIC DISTORTION AND EASE OF HYDROLYSIS IN BASE - IF AMIDIC RESONANCE DOES NOT EXIST, THEN WHAT ACCOUNTS FOR THE ACCELERATED HYDROLYSIS OF DISTORTED AMIDES[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (17) : 6383 - 6385BENNET, AJ论文数: 0 引用数: 0 h-index: 0机构: UNIV ALBERTA,DEPT CHEM,STRUCT DETERMINAT LAB,EDMONTON T6G 2G2,ALBERTA,CANADA UNIV ALBERTA,DEPT CHEM,STRUCT DETERMINAT LAB,EDMONTON T6G 2G2,ALBERTA,CANADAWANG, QP论文数: 0 引用数: 0 h-index: 0机构: UNIV ALBERTA,DEPT CHEM,STRUCT DETERMINAT LAB,EDMONTON T6G 2G2,ALBERTA,CANADA UNIV ALBERTA,DEPT CHEM,STRUCT DETERMINAT LAB,EDMONTON T6G 2G2,ALBERTA,CANADASLEBOCKATILK, H论文数: 0 引用数: 0 h-index: 0机构: UNIV ALBERTA,DEPT CHEM,STRUCT DETERMINAT LAB,EDMONTON T6G 2G2,ALBERTA,CANADA UNIV ALBERTA,DEPT CHEM,STRUCT DETERMINAT LAB,EDMONTON T6G 2G2,ALBERTA,CANADASOMAYAJI, V论文数: 0 引用数: 0 h-index: 0机构: UNIV ALBERTA,DEPT CHEM,STRUCT DETERMINAT LAB,EDMONTON T6G 2G2,ALBERTA,CANADA UNIV ALBERTA,DEPT CHEM,STRUCT DETERMINAT LAB,EDMONTON T6G 2G2,ALBERTA,CANADABROWN, RS论文数: 0 引用数: 0 h-index: 0机构: UNIV ALBERTA,DEPT CHEM,STRUCT DETERMINAT LAB,EDMONTON T6G 2G2,ALBERTA,CANADA UNIV ALBERTA,DEPT CHEM,STRUCT DETERMINAT LAB,EDMONTON T6G 2G2,ALBERTA,CANADASANTARSIERO, BD论文数: 0 引用数: 0 h-index: 0机构: UNIV ALBERTA,DEPT CHEM,STRUCT DETERMINAT LAB,EDMONTON T6G 2G2,ALBERTA,CANADA UNIV ALBERTA,DEPT CHEM,STRUCT DETERMINAT LAB,EDMONTON T6G 2G2,ALBERTA,CANADA
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- [4] Barriers to Rotation in ortho-Substituted Tertiary Aromatic Amides: Effect of Chloro-Substitution on Resonance and Distortion[J]. JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (06) : 3159 - 3163Bisz, Elwira论文数: 0 引用数: 0 h-index: 0机构: Univ Wroclaw, Dept Chem, F Joliot Curie 14, PL-50383 Wroclaw, Poland Opole Univ, Dept Chem, 48 Oleska St, PL-45052 Opole, PolandPiontek, Aleksandara论文数: 0 引用数: 0 h-index: 0机构: Univ Wroclaw, Dept Chem, F Joliot Curie 14, PL-50383 Wroclaw, Poland Opole Univ, Dept Chem, 48 Oleska St, PL-45052 Opole, PolandDziuk, Blazej论文数: 0 引用数: 0 h-index: 0机构: Univ Wroclaw, Dept Chem, F Joliot Curie 14, PL-50383 Wroclaw, Poland Opole Univ, Dept Chem, 48 Oleska St, PL-45052 Opole, PolandSzostak, Roman论文数: 0 引用数: 0 h-index: 0机构: Rutgers State Univ, Dept Chem, 73 Warren St, Newark, NJ 07102 USA Opole Univ, Dept Chem, 48 Oleska St, PL-45052 Opole, PolandSzostak, Michal论文数: 0 引用数: 0 h-index: 0机构: Opole Univ, Dept Chem, 48 Oleska St, PL-45052 Opole, Poland Univ Wroclaw, Dept Chem, F Joliot Curie 14, PL-50383 Wroclaw, Poland Opole Univ, Dept Chem, 48 Oleska St, PL-45052 Opole, Poland
- [5] Mechanism of the mild functionalization of arenes by diboron reagents catalyzed by iridium complexes. Intermediacy and chemistry of bipyridine-ligated iridium trisboryl complexes[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (41) : 14263 - 14278Boller, TM论文数: 0 引用数: 0 h-index: 0机构: Yale Univ, Dept Chem, New Haven, CT 06520 USAMurphy, JM论文数: 0 引用数: 0 h-index: 0机构: Yale Univ, Dept Chem, New Haven, CT 06520 USAHapke, M论文数: 0 引用数: 0 h-index: 0机构: Yale Univ, Dept Chem, New Haven, CT 06520 USAIshiyama, T论文数: 0 引用数: 0 h-index: 0机构: Yale Univ, Dept Chem, New Haven, CT 06520 USAMiyaura, N论文数: 0 引用数: 0 h-index: 0机构: Yale Univ, Dept Chem, New Haven, CT 06520 USAHartwig, JF论文数: 0 引用数: 0 h-index: 0机构: Yale Univ, Dept Chem, New Haven, CT 06520 USA
- [6] Noncovalent interactions of molecules with single walled carbon nanotubes[J]. CHEMICAL SOCIETY REVIEWS, 2006, 35 (07) : 637 - 659Britz, David A.论文数: 0 引用数: 0 h-index: 0机构: Univ Oxford, Dept Mat, Oxford OX1 3PH, EnglandKhlobystov, Andrei N.论文数: 0 引用数: 0 h-index: 0机构: Univ Oxford, Dept Mat, Oxford OX1 3PH, England
- [7] Remarkably selective iridium catalysts for the elaboration of aromatic C-H bonds[J]. SCIENCE, 2002, 295 (5553) : 305 - 308Cho, JY论文数: 0 引用数: 0 h-index: 0机构: Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA Michigan State Univ, Dept Chem, E Lansing, MI 48824 USATse, MK论文数: 0 引用数: 0 h-index: 0机构: Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA Michigan State Univ, Dept Chem, E Lansing, MI 48824 USAHolmes, D论文数: 0 引用数: 0 h-index: 0机构: Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA Michigan State Univ, Dept Chem, E Lansing, MI 48824 USAMaleczka, RE论文数: 0 引用数: 0 h-index: 0机构: Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA Michigan State Univ, Dept Chem, E Lansing, MI 48824 USASmith, MR论文数: 0 引用数: 0 h-index: 0机构: Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA
- [8] Steric and chelate directing effects in aromatic borylation[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (51) : 12868 - 12869Cho, JY论文数: 0 引用数: 0 h-index: 0机构: Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA Michigan State Univ, Dept Chem, E Lansing, MI 48824 USAIverson, CN论文数: 0 引用数: 0 h-index: 0机构: Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA Michigan State Univ, Dept Chem, E Lansing, MI 48824 USASmith, MR论文数: 0 引用数: 0 h-index: 0机构: Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA
- [9] Sterically directed functionalization of aromatic C-H bonds: Selective borylation ortho to cyano groups in arenes and heterocycles[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (30) : 10539 - 10544Chotana, GA论文数: 0 引用数: 0 h-index: 0机构: Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA Michigan State Univ, Dept Chem, E Lansing, MI 48824 USARak, MA论文数: 0 引用数: 0 h-index: 0机构: Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA Michigan State Univ, Dept Chem, E Lansing, MI 48824 USASmith, MR论文数: 0 引用数: 0 h-index: 0机构: Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA
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