Palladium-Catalyzed Arylation of Endocyclic 1-Azaallyl Anions: Concise Synthesis of Unprotected Enantioenriched cis-2,3-Diarylpiperidines

被引：8

作者：

Zhang, Biao ^{[1
]}

Ruan, Junhao ^{[1
]}

Seidel, Daniel ^{[2
]}

Chen, Weijie ^{[1
]}

机构：

[1] Tongji Univ, Inst Adv Studies, Sch Chem Sci & Engn, 1239 Siping Rd, Shanghai 200092, Peoples R China

[2] Univ Florida, Ctr Heterocycl Cpds, Dept Chem, Gainesville, FL 32611 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2023年 / 62卷 / 36期

关键词：

Arylation; Endocyclic 1-Azaallyl Anions; Endocyclic Imines; Palladium Catalysis; Piperidines; H BOND FUNCTIONALIZATION; ARYL-SUBSTITUTED PIPERIDINES; DYNAMIC KINETIC RESOLUTION; SATURATED CYCLIC AMINES; ENANTIOSELECTIVE SYNTHESIS; C(SP(3))-H ARYLATION; STEREOSELECTIVE-SYNTHESIS; DELTA-OXOESTERS; ALPHA-ARYLATION; C-C;

D O I：

10.1002/anie.202307638

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Unprotected cis-2,3-diarylpiperidines are synthesized through an unprecedented palladium-catalyzed cross-coupling reaction between aryl halides and elusive endocyclic 1-azaallyl anions. These intermediates are generated in situ by the deprotonation of 2-aryl-1-piperideines, precursors that are readily prepared in two operations from simple piperidines. An asymmetric version of this reaction with (2R, 3R)-iPr-BI-DIME as the ligand provides products in moderate to good yields and enantioselectivities. This study significantly expands the synthetic utility of endocyclic 1-azaallyl anions.

引用

页数：6

共 4 条

[1] Palladium-Catalyzed Allylation of Endocyclic 1-Azaallyl Anions
Yang, Xiaoyu
Zhang, Biao
Ruan, Junhao
Duanmu, Kaining
Chen, Weijie
JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (12): : 8896 - 8905
[2] Synthesis of diarylmethylamines via palladium-catalyzed regioselective arylation of 1,1,3-triaryl-2-azaallyl anions
Li, Minyan
Yucel, Baris
Adrio, Javier
Bellomo, Ana
Walsh, Patrick J.
CHEMICAL SCIENCE, 2014, 5 (06) : 2383 - 2391
[3] Palladium-Catalyzed Regioselective Arylation of 1,1,3-Triaryl-2-azaallyl Anions with Aryl Chlorides
Li, Minyan
Berritt, Simon
Walsh, Patrick J.
ORGANIC LETTERS, 2014, 16 (16) : 4312 - 4315
[4] Palladium-Catalyzed Arylation of Cyclopropanes via Directing Group-Mediated C(sp3)-H Bond Activation To Construct Quaternary Carbon Centers: Synthesis of cis- and trans-1,1,2-Trisubstituted Chiral Cyclopropanes
Hoshiya, Naoyuki
Kobayashi, Takaaki
Arisawa, Mitsuhiro
Shuto, Satoshi
ORGANIC LETTERS, 2013, 15 (24) : 6202 - 6205

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