Intramolecular Pd-Catalyzed Anomeric C(sp3)-H Activation of Glycosyl Carboxamides

被引：36

作者：

Probst, Nicolas ^{[1
]}

Grelier, Gwendal ^{[2
]}

Gherman, NourEddine ^{[3
]}

Gandon, Vincent ^{[2
,4
]}

Alami, Mouad ^{[1
]}

Messaoudi, Samir ^{[1
]}

机构：

[1] Univ Paris Saclay, Univ Paris Sud, CNRS, BioCIS, Chatenay Malabry, France

[2] Univ Paris Saclay, Univ Paris Sud, CNRS UPR 2301, Inst Chim Subst Nat, 1 Av Terrasse, F-91198 Gif Sur Yvette, France

[3] Univ Paris Saclay, Univ Sud, CNRS, Inst Galien, F-92296 Chatenay Malabry, France

[4] Univ Paris Saclay, Univ Paris Sud, CNRS UMR 8182, Inst Chim Mol & Mat Orsay, F-91405 Orsay, France

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 19期

关键词：

C-H BONDS; CYCLOISOMERIZATION REACTIONS; ARYLBORONIC ACIDS; DIRECT ARYLATION; ALPHA-ARYLATION; PALLADIUM; LIGAND; RECOGNITION; FUNCTIONALIZATIONS; ALKENYLATION;

D O I：

10.1021/acs.orglett.7b02170

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An expedient method for the synthesis of fused glycosylquinolin-2-ones and glycosylspirowandoles through an unprecedented intramolecular Pd-catalyzed anomeric C-H activation of the sugar moiety of 2-bromophenyl glycosylcarboxamides is reported. The scope of the reaction is broad and tolerates a wide range of functional groups.

引用

页码：5038 / 5041

页数：4

共 50 条

[21] Pd-catalyzed bidentate auxiliary assisted remote C(sp3)-H functionalization
Talukdar, Kangkan
Shah, Tariq A.
Sarkar, Tanumay
Roy, Subhasish
Maharana, Prabhat Kumar
Punniyamurthy, Tharmalingam
CHEMICAL COMMUNICATIONS, 2021, 57 (98) : 13221 - 13233
[22] Palladium-Catalyzed Unactivated C(sp3)-H Bond Activation and intramolecular Amination of Carboxamides: A New Approach to β-Lactams
Sun, Wen-Wu
Cao, Pei
Mei, Ren-Qiang
Li, Yue
Ma, Yuan-Liang
Wu, Bin
ORGANIC LETTERS, 2014, 16 (02) : 480 - 483
[23] The Direct Pd-Catalyzed -C(sp 3 )-H Activation of Carboxylic Acids
Uttry, Alexander
van Gemmeren, Manuel
SYNLETT, 2018, 29 (15) : 1937 - 1943
[24] β-Arylation of carboxamides via iron-catalyzed C(sp3)-H bond activation
Nakamura, E. (nakamura@chem.s.u-tokyo.ac.jp), 1600, American Chemical Society (135):
[25] β-Arylation of Carboxamides via Iron-Catalyzed C(sp3)-H Bond Activation
Shang, Rui
Ilies, Laurean
Matsumoto, Arimasa
Nakamura, Eiichi
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (16) : 6030 - 6032
[26] Mechanistic Study of Enantioselective Pd-Catalyzed C(sp3)-H Activation of Thioethers Involving Two Distinct Stereomodels
Saint-Denis, Tyler G.
Lam, Nelson Y. S.
Chekshin, Nikita
Richardson, Paul F.
Chen, Jason S.
Elleraas, Jeff
Hesp, Kevin D.
Schmitt, Daniel C.
Lian, Yajing
Huh, Chan Woo
Yu, Jin-Quan
ACS CATALYSIS, 2021, 11 (15) : 9738 - 9753
[27] Assembly of Tetrahydroquinolines and 2-Benzazepines by Pd-Catalyzed Cycloadditions Involving the Activation of C(sp3)-H Bonds
Vidal, Xandro
Mascarenas, Jose Luis
Gulias, Moises
ORGANIC LETTERS, 2021, 23 (14) : 5323 - 5328
[28] Asymmetric Cascade (4+1) Annulations via Pd-Catalyzed Allylic C(sp3)-H Activation
Zhang, Honghao
Shi, Feng
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (01) : 318 - 320
[29] Site-Selective Pd-Catalyzed C(sp3)−H Arylation of Heteroaromatic Ketones
Kudashev, Anton
Baudoin, Olivier
Chemistry - A European Journal, 2021, 27 (70): : 17688 - 17694
[30] Site-Selective Pd-Catalyzed C(sp3)-H Arylation of Heteroaromatic Ketones
Kudashev, Anton
Baudoin, Olivier
CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (70) : 17688 - 17694

← 1 2 3 4 5 →