Cobalt-Catalyzed α-Alkylation of Ketones with Primary Alcohols

被引：180

作者：

Zhang, Guoqi ^{[1
,2
]}

Wu, Jing ^{[1
,2
,3
]}

Zeng, Haisu ^{[1
,2
,3
]}

Zhang, Shu ^{[1
,2
]}

Yin, Zhiwei ^{[1
,2
,3
]}

Zheng, Shengping ^{[3
]}

机构：

[1] CUNY, Grad Ctr, Dept Sci, John Jay Coll, New York, NY 10019 USA

[2] CUNY, Grad Ctr, PhD Program Chem, New York, NY 10019 USA

[3] CUNY Hunter Coll, Dept Chem, New York, NY 10065 USA

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 05期

基金：

美国国家科学基金会;

关键词：

ASYMMETRIC TRANSFER HYDROGENATION; MILD REACTION CONDITIONS; ASTERISK-LR COMPLEX; C BOND FORMATION; AROMATIC-AMINES; N-ALKYLATION; SELECTIVE HYDROGENATION; IRIDIUM CATALYSTS; BRANCHED PRODUCTS; PINCER COMPLEXES;

D O I：

10.1021/acs.orglett.7b00106

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An ionic cobalt-PNP complex is developed for the efficient alpha-alkylation of ketones with primary alcohols for the first time. A broad range of ketone and alcohol substrates were employed, leading to the isolation of alkylated ketones with yields up to 98%. The method was successfully applied to the greener synthesis of quinoline derivatives while using 2-aminobenzyl alcohol as an alkylating reagent.

引用

页码：1080 / 1083

页数：4

共 50 条

[1] Cobalt-Catalyzed Alkylation of Nitriles with Alcohols
Singh, Arpita
Findlater, Michael
[J]. ORGANOMETALLICS, 2021, 41 (22) : 3145 - 3151
[2] Switchable Cobalt-Catalyzed α-Olefination and α-Alkylation of Nitriles with Primary Alcohols
Paudel, Keshav
Xu, Shi
Ding, Keying
[J]. ORGANIC LETTERS, 2021, 23 (13) : 5028 - 5032
[3] Cobalt-Catalyzed Alkylation of Aromatic Amines by Alcohols
Roesler, Sina
Ertl, Michael
Irrgang, Torsten
Kempe, Rhett
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (50) : 15046 - 15050
[4] Selective Ketone Formations via Cobalt-Catalyzed β-Alkylation of Secondary Alcohols with Primary Alcohols
Pandey, Bedraj
Xu, Shi
Ding, Keying
[J]. ORGANIC LETTERS, 2019, 21 (18) : 7420 - 7423
[5] Cobalt-Catalyzed N-Alkylation of Amines with Alcohols
Zhang, Guoqi
Yin, Zhiwei
Zheng, Shengping
[J]. ORGANIC LETTERS, 2016, 18 (02) : 300 - 303
[6] Cobalt-Catalyzed Alkylation of Secondary Alcohols with Primary Alcohols via Borrowing Hydrogen/Hydrogen Autotransfer
Freitag, Frederik
Irrgang, Torsten
Kempe, Rhett
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (50) : 12110 - 12113
[7] Cobalt-Catalyzed Reductive Deoxygenation of Aldehydes, Ketones, Alcohols, and Ethers to Alkanes
Kumar, Anurag
Pattanaik, Sandip
Joshi, Gaurav
Sahu, Manas Kumar
Jemmis, Eluvathingal D.
Gunanathan, Chidambaram
[J]. ACS CATALYSIS, 2024, 14 (06) : 4249 - 4264
[8] Cobalt-Catalyzed Efficient Asymmetric Hydrogenation of α-Primary Amino Ketones
Yang, Huiwen
Hu, Yanhua
Zou, Yashi
Zhang, Zhenfeng
Zhang, Wanbin
[J]. JACS AU, 2023, 3 (11): : 2981 - 2986
[9] A palladium-catalyzed route for α-alkylation of ketones by primary alcohols
Cho, CS
[J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2005, 240 (1-2) : 55 - 60
[10] Ruthenium-catalyzed regioselective α-alkylation of ketones with primary alcohols
Cho, CS
Kim, BT
Kim, TJ
Shim, SC
[J]. TETRAHEDRON LETTERS, 2002, 43 (44) : 7987 - 7989

← 1 2 3 4 5 →