Nickel-Catalyzed Selective Synthesis of α-Alkylated Ketones via Dehydrogenative Cross-Coupling of Primary and Secondary Alcohols

被引：26

作者：

Bains, Amreen K. ^{[1
]}

Biswas, Ayanangshu ^{[1
]}

Adhikari, Debashis ^{[1
]}

机构：

[1] Indian Inst Sci Educ & Res IISER Mohali, Dept Chem Sci, Sas Nagar 140306, Punjab, India

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2022年 / 364卷 / 01期

关键词：

nickel catalysis; cross-coupling; secondary alcohols; radical reaction; METHYLATION; QUINOLINE; METHANOL; CAMPHOR; AMIDES;

D O I：

10.1002/adsc.202101077

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Herein, we describe an isolable, air-stable, homogeneous, nickel catalyst that performs dehydrogenative cross-coupling reaction between secondary and primary alcohols to result alpha-alkylated ketone products selectively. The sequence of steps involve in this one-pot reaction is dehydrogenation of both alcohols, condensation between the ketone and the aldehyde, and hydrogenation of the in situ-generated alpha,beta-unsaturated ketone. Preliminary mechanistic investigation hints a radical mechanism following borrowing hydrogen reaction.

引用

页码：47 / 52

页数：6

共 56 条

[1] Alcohols for the α-Alkylation of Methyl Ketones and Indirect Aza-Wittig Reaction Promoted by Nickel Nanoparticles [J].

Alonso, Francisco ;

Riente, Paola ;

Yus, Miguel .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (29) :4908-4914

[2] Nickel: The "Spirited Horse" of Transition Metal Catalysis [J].

Ananikov, Valentine P. .

ACS CATALYSIS, 2015, 5 (03) :1964-1971

[3]

[Anonymous], 2014, Angew. Chem, V126, P780

[4]

[Anonymous], 2015, ANGEW CHEM, V127, P14691

[5] Pincer-Nickel Catalyzed Selective Guerbet-Type Reactions [J].

Arora, Vinay ;

Narjinari, Himani ;

Kumar, Akshai .

ORGANOMETALLICS, 2021, 40 (16) :2870-2880

[6] Nickel-Catalyzed Dehydrogenative Couplings [J].

Arun, V ;

Mahanty, Kingshuk ;

De Sarkar, Suman .

CHEMCATCHEM, 2019, 11 (09) :2243-2259

[7] Nickel-Catalyzed Guerbet Type Reaction: C-Alkylation of Secondary Alcohols via Double (de)Hydrogenation [J].

Babu, Reshma ;

Subaramanian, Murugan ;

Midya, Siba P. ;

Balaraman, Ekambaram .

ORGANIC LETTERS, 2021, 23 (09) :3320-3325

[8] Nickel-catalysed chemoselective C-3 alkylation of indoles with alcohols through a borrowing hydrogen method [J].

Bains, Amreen K. ;

Biswas, Ayanangshu ;

Adhikari, Debashis .

CHEMICAL COMMUNICATIONS, 2020, 56 (98) :15442-15445

[9] Homogeneous Nickel-Catalyzed Sustainable Synthesis of Quinoline and Quinoxaline under Aerobic Conditions [J].

Bains, Amreen K. ;

Singh, Vikramjeet ;

Adhikari, Debashis .

JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (23) :14971-14979

[10] Nickel catalysed construction of benzazolesviahydrogen atom transfer reactions [J].

Bains, Amreen K. ;

Dey, Dhananjay ;

Yadav, Sudha ;

Kundu, Abhishek ;

Adhikari, Debashis .

CATALYSIS SCIENCE & TECHNOLOGY, 2020, 10 (19) :6495-6500

← 1 2 3 4 5 6 →