Nickel-catalyzed C3-alkylation of indoles with alcohols via a borrowing hydrogen strategy

被引：25

作者：

Hu, Miao ^{[1
]}

Jiang, Yong ^{[1
]}

Sun, Nan ^{[1
]}

Hu, Baoxiang ^{[1
]}

Shen, Zhenlu ^{[1
]}

Hu, Xinquan ^{[1
]}

Jin, Liqun ^{[1
,2
]}

机构：

[1] Zhejiang Univ Technol, Coll Chem Engn, Hangzhou 310032, Peoples R China

[2] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China

来源：

NEW JOURNAL OF CHEMISTRY | 2021年 / 45卷 / 22期

关键词：

C BOND FORMATION; ALPHA-ALKYLATION; UNACTIVATED AMIDES; KETONES; METHYLATION; ESTERS; ARYLACETONITRILES; FUNCTIONALIZATION; COMPLEXES; METHANOL;

D O I：

10.1039/d1nj01581h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient method for the Ni-catalyzed C3-alkylation of indoles using readily available alcohols as the alkylating reagents has been developed. The alkylation was addressed with an air and moisture-stable binuclear nickel complex ligated by tetrahydroquinolin-8-one as the effective pre-catalyst. The newly developed transformation could accommodate a broad substrate scope including primary/secondary benzylic and aliphatic alcohols and substituted indoles. Mechanistic studies suggested that the reaction proceeds through a borrowing hydrogen pathway.

引用

页码：10057 / 10062

页数：6

共 65 条

[11] An unusual type of ruthenium-catalyzed transfer hydrogenation of ketones with alcohols accompanied by C-C coupling
Cho, CS
Kim, BT
Kim, TJ
Shim, SC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (26) : 9020 - 9022
[12] Advances in One-Pot Synthesis through Borrowing Hydrogen Catalysis
Corma, Avelino
Navas, Javier
Sabater, Maria J.
[J]. CHEMICAL REVIEWS, 2018, 118 (04) : 1410 - 1459
[13] Nickel-Catalyzed Hydrogen-Borrowing Strategy for α-Alkylation of Ketones with Alcohols: A New Route to Branched gem-Bis(alkyl) Ketones
Das, Jagadish
Singh, Khushboo
Vellakkaran, Mari
Banerjee, Debasis
[J]. ORGANIC LETTERS, 2018, 20 (18) : 5587 - 5591
[14] Novel N-Acetyl Bioisosteres of Melatonin: Melatonergic Receptor Pharmacology, Physicochemical Studies, and Phenotypic Assessment of Their Neurogenic Potential
de la Fuente Revenga, Mario
Fernandez-Saez, Nerea
Herrera-Arozamena, Clara
Morales-Garcia, Jose A.
Alonso-Gil, Sandra
Perez-Castillo, Ana
Caignard, Daniel-Henri
Rivara, Silvia
Isabel Rodriguez-Franco, Maria
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2015, 58 (12) : 4998 - 5014
[15] General and Mild Cobalt-Catalyzed C-Alkylation of Unactivated Amides and Esters with Alcohols
Deibl, Nicklas
Kempe, Rhett
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (34) : 10786 - 10789
[16] Recent Advances on the C2-Functionalization of Indole via Umpolung
Deka, Bhaskar
Deb, Mohit L.
Baruah, Pranjal K.
[J]. TOPICS IN CURRENT CHEMISTRY, 2020, 378 (02)
[17] Iron-Catalyzed Direct C3-Benzylation of Indoles with Benzyl Alcohols through Borrowing Hydrogen
Di Gregorio, Giovanni
Mari, Michele
Bartoccini, Francesca
Piersanti, Giovanni
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (16) : 8769 - 8775
[18] Iron-Catalyzed α-Alkylation of Ketones with Alcohols
Elangovan, Saravanakumar
Sortais, Jean-Baptiste
Beller, Matthias
Darcel, Christophe
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (48) : 14483 - 14486
[19] Synthetic Applications Based on Dehydrogenative Alcohol Activation Catalyzed by Mn-, Fe and Co-complexes
Ferraccioli, Raffaella
[J]. CURRENT ORGANIC CHEMISTRY, 2018, 22 (19) : 1875 - 1892
[20] Bidentate Ru(II)-NC Complexes as Catalysts for α-Alkylation of Unactivated Amides and Esters
Gong, Dawei
Hu, Bowen
Yang, Weiwei
Chen, Dafa
[J]. CHEMCATCHEM, 2019, 11 (19) : 4841 - 4847

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