Ni-Catalyzed Allylic Dearomatization Reaction of β-Naphthols with Allylic Alcohols

被引：26

作者：

Zhang, Hui-Jun ^{[1
]}

Gu, Qing ^{[2
]}

You, Shu-Li ^{[1
,2
]}

机构：

[1] East China Univ Sci & Technol, Sch Chem & Mol Engn, Shanghai 200237, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 08期

基金：

国家重点研发计划;

关键词：

CROSS-COUPLING REACTIONS; ASYMMETRIC DEAROMATIZATION; GRIGNARD-REAGENTS; ENANTIOSELECTIVE DEAROMATIZATION; INTRAMOLECULAR DEAROMATIZATION; SUBSTITUTION-REACTIONS; BOND FORMATION; ALKYLATION; ALLYLATION; PALLADIUM;

D O I：

10.1021/acs.orglett.0c01109

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ni-catalyzed intermolecular allylic dearomatization reaction of beta-naphthols with allylic alcohols was achieved. By utilizing Ni(cod)(2) as a catalyst precursor, DPEphos as a ligand and 4 angstrom molecular sieves as additives, the dearomatization reaction of beta-naphthols with aryl allylic alcohols proceeded smoothly under mild conditions, affording the desired beta-naphthalenone products bearing a quaternary carbon center in moderate to good yields with excellent linear selectivity.

引用

页码：3297 / 3301

页数：5

共 50 条

[21] Ni-Catalyzed Reductive Allylation of Unactivated Alkyl Halides with Allylic Carbonates
Dai, Yijing
Wu, Fan
Zang, Zhenhua
You, Hengzhi
Gong, Hegui
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (03) : 808 - 812
[22] Iodine-catalyzed allylic alkylation of thiols with allylic alcohols
Zhang, Xiaoxiang
Rao, Weidong
Chan, Philip Wai Hong
SYNLETT, 2008, (14) : 2204 - 2208
[23] ALLYLIC ALCOHOLS AS SUBSTRATES FOR THE PALLADIUM(0)-CATALYZED ALLYLIC SUBSTITUTION
STARY, I
STARA, IG
KOCOVSKY, P
TETRAHEDRON LETTERS, 1993, 34 (01) : 179 - 182
[24] Palladium-Catalyzed Intermolecular Asymmetric Allylic Dearomatization Reaction of Naphthol Derivatives
Zhuo, Chun-Xiang
You, Shu-Li
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (38) : 10056 - 10059
[25] Ruthenium-Catalyzed Intramolecular Allylic Dearomatization/Migration Reaction of Indoles and Pyrroles
Yang, Ze-Peng
Zhuo, Chun-Xiang
You, Shu-Li
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (08) : 1731 - 1734
[26] Direct use of allylic alcohols and allylic amines in palladium-catalyzed allylic amination
Jing, Jiangyan
Huo, Xiaohong
Shen, Jiefeng
Fu, Jingke
Meng, Qinghua
Zhang, Wanbin
CHEMICAL COMMUNICATIONS, 2017, 53 (37) : 5151 - 5154
[27] Asymmetric Cascade Reaction to Allylic Sulfonamides from Allylic Alcohols by Palladium(II)/Base-Catalyzed Rearrangement of Allylic Carbamates
Bauer, Johannes Moritz
Frey, Wolfgang
Peters, Rene
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (29) : 7634 - 7638
[28] REACTION OF NBS WITH ALLYLIC ALCOHOLS
ROMERO, MA
JOURNAL OF ORGANIC CHEMISTRY, 1957, 22 (10): : 1267 - 1268
[29] From allylic alcohols to aldols via a novel, efficient reaction catalyzed by Ni-complexes
Cuperly, D
Crévisy, C
Grée, R
SYNLETT, 2004, (01) : 93 - 96
[30] Ni-catalyzed regioselective and site-divergent reductive arylalkylations of allylic amines
Meng, Huan
Jia, Jun-Song
Yang, Peng-Fei
Li, Yu-Long
Yu, Qiong
Shu, Wei
CHEMICAL SCIENCE, 2025, 16 (10) : 4442 - 4449

← 1 2 3 4 5 →