Room Temperature Metal-Catalyzed Oxidative Acylation of Electron-Deficient Heteroarenes with Alkynes, Its Mechanism, and Application Studies

被引：24

作者：

Sharma, Shweta ^{[1
]}

Kumar, Mukesh ^{[1
]}

Vishwakarma, Ram A. ^{[1
]}

Verma, Mahendra K. ^{[2
]}

Singh, Parvinder Pal ^{[1
]}

机构：

[1] Indian Inst Integrat Med, CSIR, Acad Sci & Innovat Res, Div Med Chem, Canal Rd, Jammu 180001, India

[2] Indian Inst Integrat Med, CSIR, Div Analyt Chem, Canal Rd, Jammu 180001, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 20期

关键词：

FREE-RADICAL REACTIONS; ALPHA-KETO ACIDS; N-OXIDES; DECARBOXYLATIVE ACYLATION; HOMOLYTIC ACYLATION; TERMINAL ALKYNES; HETEROCYCLES; ALKALOIDS; ALDEHYDES; AMIDES;

D O I：

10.1021/acs.joc.8b01475

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we report an original one-step, simple, room-temperature, regioselective Minisci reaction for the acylation of electron-deficient heteroarenes with alkynes. The method has broad functional group compatibility and gives exclusively monoacylated products in good to excellent yields. The mechanistic pathway was analyzed based on a series of experiments confirming the involvement of a radical pathway. The O-18-labeling experiment suggested that water is a source of oxygen in the acylated product, and head space GC MS experiment shows the C-C cleavage occurs via release as CO2.

引用

页码：12420 / 12431

页数：12

共 55 条

[1] Metal-Free, Phosphonium Salt-Mediated Sulfoximination of Azine N-Oxides: Approach for the Synthesis of N-Azine Sulfoximines [J].

Aithagani, Sravan Kumar ;

Kumar, Mukesh ;

Yadav, Mahipal ;

Vishwakarma, Ram A. ;

Singh, Parvinder Pal .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (14) :5886-5894

[2] Regiospecific Benzoylation of Electron-Deficient N-Heterocycles with Methylbenzenes via a Minisci-Type Reaction [J].

Ali, Wajid ;

Behera, Ahalya ;

Guin, Srimanta ;

Patel, Bhisma K. .

JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (11) :5625-5632

[3] THE SYNTHESIS OF THALMICRINONE, A CONFIRMATION OF STRUCTURE [J].

ALKHALIL, S ;

SCHIFF, PL .

JOURNAL OF NATURAL PRODUCTS, 1985, 48 (06) :989-991

[4] Cross-dehydrogenative coupling of α-C(sp3)-H of ethers/alkanes with C(sp2)-H of heteroarenes under metal-free conditions [J].

Ambala, Srinivas ;

Thatikonda, Thanusha ;

Sharma, Shweta ;

Munagala, Gurunadham ;

Yempalla, Kushalava Reddy ;

Vishwakarma, Ram A. ;

Singh, Parvinder Pal .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (46) :11341-11350

[5] Metal-free Cross-Dehydrogenative Coupling of HN-azoles with α-C(sp3)-H Amides via C-H Activation and Its Mechanistic and Application Studies [J].

Aruri, Hariprasad ;

Singh, Umed ;

Kumar, Mukesh ;

Sharma, Sumit ;

Aithagani, Sravan Kumar ;

Gupta, Vivek K. ;

Mignani, Serge ;

Vishwakarma, Ram A. ;

Singh, Parvinder Pal .

JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (02) :1000-1012

[6] I2/Aqueous TBHP-Catalyzed Coupling of Amides with Methylarenes/Aldehydes/Alcohols: Metal-Free Synthesis of Imides [J].

Aruri, Hariprasad ;

Singh, Umed ;

Kumar, Sanjay ;

Kushwaha, Manoj ;

Gupta, Ajai Prakash ;

Vishwakarma, Ram A. ;

Singh, Parvinder Pal .

ORGANIC LETTERS, 2016, 18 (15) :3638-3641

[7] ISOLATION AND IDENTIFICATION OF ANISALDEHYDE AND 3 ALKALOIDS FROM LEAVES OF THALICTRUM-MINUS VAR MICROPHYLLUM [J].

BASER, KHC .

JOURNAL OF NATURAL PRODUCTS, 1982, 45 (06) :704-706

[8]

BOLAND ME, 1985, LANCET, V1, P384

[9] Transition Metal-Mediated Direct C-H Arylation of Heteroarenes Involving Aryl Radicals [J].

Bonin, Helene ;

Sauthier, Mathieu ;

Felpin, Francois-Xavier .

ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (04) :645-671

[10] Regiospecific Acylation of Cycloplatinated Complexes: Scope, Limitations, and Mechanistic Implications [J].

Carroll, Jeffrey ;

Woolard, Hannah G. ;

Mroz, Robert ;

Nason, Charles A. ;

Huo, Shouquan .

ORGANOMETALLICS, 2016, 35 (09) :1313-1322

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