Phosphine oxide directing-group-enabled atroposelective C-H bond acyloxylation via an eight-membered palladacycle intermediate

被引：17

作者：

Bai, Peng-Bo ^{[1
]}

Wu, Ming-Ying ^{[1
]}

Yang, Xin-Xin ^{[1
]}

Wang, Gang-Wei ^{[1
]}

Yang, Shang-Dong ^{[1
,2
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

[2] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China

来源：

CHINESE CHEMICAL LETTERS | 2023年 / 34卷 / 05期

关键词：

Palladiumcatalyst; Axially chiral; Acetylation; Dibenzophosphorus oxide; ALPHA-AMINO-ACID; ORGANOPHOSPHORUS COMPOUNDS; CATALYZED OXIDATION; RAPID CONSTRUCTION; COUPLING REACTIONS; FUNCTIONALIZATION; ACETOXYLATION; C(SP(2))-H; ACTIVATION; ARYLATION;

D O I：

10.1016/j.cclet.2022.107894

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein, we report the first atroposelective C(sp2)-H bond acyloxylation enabled by a phosphine oxide di-recting group. Uniquely, this transformation is shown to proceed through an eight-membered palladacycle intermediate, as opposed to the kinetically and thermodynamically favored five-membered palladacycle intermediate. Additionally, L-pGlu-OH, a cheap and abundant chiral amino acid derivative, was identified as the best chiral ligand to promote this atroposelective remote C -H functionalization reaction. (c) 2023 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.

引用

页数：4

共 79 条

[11] Enantiodivergent Kinetic Resolution of 1,1′-Biaryl-2,2′-Diols and Amino Alcohols by Dipeptide-Phosphonium Salt Catalysis Inspired by the Atherton-Todd Reaction [J].

Fang, Siqiang ;

Tan, Jian-Ping ;

Pan, Jianke ;

Zhang, Hongkui ;

Chen, Yuan ;

Ren, Xiaoyu ;

Wang, Tianli .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (27) :14921-14930

[12] Catalytic Atroposelective Catellani Reaction Enables Construction of Axially Chiral Biaryl Monophosphine Oxides [J].

Feng, Qiang ;

Ma, Xingxing ;

Bao, Wen ;

Li, Shi-Jun ;

Lan, Yu ;

Song, Qiuling .

CCS CHEMISTRY, 2021, 3 (12) :377-387

[13] The Cross-Dehydrogenative Coupling of Csp3-H Bonds: A Versatile Strategy for C-C Bond Formations [J].

Girard, Simon A. ;

Knauber, Thomas ;

Li, Chao-Jun .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (01) :74-100

[14] Recent advances of allenes in the first-row transition metals catalyzed C-H activation reactions [J].

Han, Xiang-Lei ;

Lin, Peng-Peng ;

Li, Qingjiang .

CHINESE CHEMICAL LETTERS, 2019, 30 (08) :1495-1502

[15] Palladium-Catalyzed Transformations of Alkyl C-H Bonds [J].

He, Jian ;

Wasa, Masayuki ;

Chan, Kelvin S. L. ;

Shao, Ojan ;

Yu, Jin-Quan .

CHEMICAL REVIEWS, 2017, 117 (13) :8754-8786

[16] PALLADIUM(II)-CATALYZED AROMATIC SUBSTITUTION [J].

HENRY, PM .

JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (14) :1886-&

[17] Cross-Dehydrogenative Coupling Reactions Between P(O)-H and X-H (X = S, N, O, P) Bonds [J].

Hosseinian, Akram ;

Farshbaf, Sepideh ;

Fekri, Leila Zare ;

Nikpassand, Mohammad ;

Vessally, Esmail .

TOPICS IN CURRENT CHEMISTRY, 2018, 376 (03)

[18] Palladium-catalyzed P(O)R2 directed C-H arylation to synthesize electron-rich polyaromatic monophosphorus ligands [J].

Hu, Rong-Bin ;

Zhang, Heng ;

Zhang, Xiao-Yu ;

Yang, Shang-Dong .

CHEMICAL COMMUNICATIONS, 2014, 50 (17) :2193-2195

[19] Recent Advances in the Total Synthesis of Natural Products Containing Eight-Membered Carbocycles (2009-2019) [J].

Hu, Ya-Jian ;

Li, Li-Xuan ;

Han, Jing-Chun ;

Min, Long ;

Li, Chuang-Chuang .

CHEMICAL REVIEWS, 2020, 120 (13) :5910-5953

[20] Enantioselective Synthesis of Indole-Annulated Medium-Sized Rings [J].

Huang, Lin ;

Dai, Li-Xin ;

You, Shu-Li .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (18) :5793-5796

← 1 2 3 4 5 6 7 8 →