Enantioselective Intermolecular Benzylic C-H Amination under Chiral Paddle-Wheel Diruthenium Catalysis

被引：1

作者：

Makino, Kotoko ^{[1
,2
]}

Mori, Kohei ^{[1
,2
]}

Kiryu, Shoichi ^{[1
]}

Miyazawa, Taku ^{[1
]}

Kumagai, Yuhei ^{[1
]}

Higashida, Kosuke ^{[2
]}

Kojima, Masahiro ^{[1
]}

Yoshino, Tatsuhiko ^{[2
,3
]}

Matsunaga, Shigeki ^{[1
,2
]}

机构：

[1] Hokkaido Univ, Fac Pharmaceut Sci, Sapporo 0600812, Japan

[2] Kyoto Univ, Grad Sch Sci, Kyoto 6068502, Japan

[3] Kyoto Univ, Hakubi Ctr Adv Res, Kyoto 6068502, Japan

来源：

ACS CATALYSIS | 2024年 / 15卷 / 01期

基金：

日本学术振兴会;

关键词：

Ruthenium catalysis; Asymmetric catalysis; Nitrene; C-H amination; Chemoselectivity; NITROGEN-ATOM TRANSFER; C(SP(3))-H AMINATION; DIRHODIUM TETRACARBOXYLATES; STEREOSELECTIVE-SYNTHESIS; BISMUTH-RHODIUM; BONDS; RUTHENIUM; AZIRIDINATIONS; FUNCTIONALIZATION; AMIDATION;

D O I：

10.1021/acscatal.4c06504

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A catalytic asymmetric intermolecular benzylic C-H amination was achieved under paddle-wheel diruthenium catalysis. A chiral diruthenium catalyst incorporating (S)-TPPTTL (tetraphenylphthaloyl-(S)-tert-leucine) ligand exhibited notable enantioselectivity, and aminated products were obtained with up to 99% ee. Unique chemoselectivity of the chiral diruthenium catalyst was also found for allylbenzene and alkyl-naphthalene substrates, demonstrating the complementary synthetic utility of chiral paddle-wheel Ru(II)-Ru(III) catalysts to Rh(II) counterparts.

引用

页码：523 / 528

页数：6

共 50 条

[41] Role of Engineered Iron-haem Enzyme in Reactivity and Stereoselectivity of Intermolecular Benzylic C-H Bond Amination
Wang, Juping
Gao, Hui
Yang, Lijiang
Gao, Yi Qin
ACS CATALYSIS, 2020, 10 (09) : 5318 - 5327
[42] Mn(salen)-catalyzed enantioselective C-H amination
Kohmura, Y
Katsuki, T
TETRAHEDRON LETTERS, 2001, 42 (19) : 3339 - 3342
[43] Intermolecular Radical C(sp3)-H Amination under Iodine Catalysis
Bosnidou, Alexandra E.
Muniz, Kilian
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (22) : 7485 - 7489
[44] Benzothiazole-Directed Enantioselective Borylation of Secondary Benzylic C-H Bonds Using Iridium Catalysis
Xie, Liang-Jun
Chen, Lili
Xu, Senmiao
SYNTHESIS-STUTTGART, 2024, 56 (17): : 2638 - 2647
[45] Manganese-Catalyzed Enantioselective Benzylic C-H Azidation
Yilitabaier, Julaiti
Xie Jin
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (11) : 3901 - 3902
[46] Electrochemical Benzylic C-H Amination via N-Aminopyridinium
Liu, Jingwei
Du, Jinyao
Zhang, Lin-Bao
Li, Ming
Guo, Weisi
JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (09): : 6465 - 6473
[47] Acyclic Stereocontrol in the Catalytic C-H Amination of Benzylic Methylene Groups
Noerder, Anike
Herrmann, Pavel
Herdtweck, Eberhard
Bach, Thorsten
ORGANIC LETTERS, 2010, 12 (16) : 3690 - 3692
[48] Enantioselective hydroxylation of benzylic C-H bonds by D4-symmetric chiral oxoruthenium porphyrins
Zhang, R
Yu, WY
Lai, TS
Che, CM
CHEMICAL COMMUNICATIONS, 1999, (18) : 1791 - 1792
[49] Pd-Catalyzed Intermolecular C-H Amination with Alkylamines
Yoo, Eun Jeong
Ma, Sandy
Mei, Tian-Sheng
Chan, Kelvin S. L.
Yu, Jin-Quan
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (20) : 7652 - 7655
[50] Silver-catalyzed intermolecular amination of C-H groups
Li, Zigang
Capretto, D. A.
Rahaman, R.
He, Chuan
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (27) : 5184 - 5186

← 1 2 3 4 5 →