Hydrogen Transfer Coupling with 100% Atom Economy: Synthesis of 2‑Indolyltetrahydronaphthyridine Derivatives

An iridium-catalyzed hydrogen transfer strategy, enabling straightforward access to tetrahydropyridine derivatives from aryl-1,8-naphthyridines and indolines was developed. This method has unprecedented advantages, including high step economy. In addition, it does not produce any byproducts or requi...

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Published inJournal of organic chemistry Vol. 87; no. 18; pp. 12257 - 12264
Main Authors Zeng, Zheng, Deng, Yiqiu, Li, Lanyu, Li, Chungang, Zhong, Mingli
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.09.2022
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
HETEROARENES
AMINATION
HETEROCYCLES
IRIDIUM
AMINES
IMINES
COMPLEXES
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Abstract An iridium-catalyzed hydrogen transfer strategy, enabling straightforward access to tetrahydropyridine derivatives from aryl-1,8-naphthyridines and indolines was developed. This method has unprecedented advantages, including high step economy. In addition, it does not produce any byproducts or require an external high-pressure H2 gas source. The method offers an important platform for the transformation of 1,8-naphthyridines and indolines into functionalized products.
AbstractList An iridium-catalyzed hydrogen transfer strategy, enabling straightforward access to tetrahydropyridine derivatives from aryl-1,8-naphthyridines and indolines was developed. This method has unprecedented advantages, including high step economy. In addition, it does not produce any byproducts or require an external high-pressure H2 gas source. The method offers an important platform for the transformation of 1,8-naphthyridines and indolines into functionalized products.
An iridium-catalyzed hydrogen transfer strategy, enabling straightforward access to tetrahydropyridine derivatives from aryl-1,8-naphthyridines and indolines was developed. This method has unprecedented advantages, including high step economy. In addition, it does not produce any byproducts or require an external high-pressure H-2 gas source. The method offers an important platform for the transformation of 1,8-naphthyridines and indolines into functionalized products.
Author Deng, Yiqiu
Li, Chungang
Li, Lanyu
Zeng, Zheng
Zhong, Mingli
AuthorAffiliation The 926th Hospital of the Joint Logistics Support Force of the Chinese People’s Liberation Army
Guilin Medical University
College of Pharmacy
College of Biological and Chemical Engineering
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Cites_doi 10.1021/ja408149n
10.1002/anie.201507955
10.1039/c9sc00595a
10.1016/j.jcat.2020.09.036
10.1021/acs.orglett.0c02924
10.1002/anie.201300292
10.1002/anie.201608345
10.1002/cctc.201601307
10.1021/ja072371m
10.1021/acs.chemrev.8b00306
10.1039/c1cc10507h
10.1039/c7sc02578e
10.1002/anie.201500346
10.1016/j.bmcl.2003.11.036
10.1002/anie.201409246
10.1002/adsc.202101098
10.1021/acs.chemrev.8b00404
10.1016/j.jcat.2021.08.037
10.1021/acs.joc.9b02558
10.1016/j.jcat.2021.08.038
10.1021/om010523v
10.1021/om070170l
10.1021/acs.orglett.0c01648
10.1016/j.isci.2020.101003
10.1021/ol501259q
10.1039/C7SC02578E
10.1002/ange.201500346
10.1021/ja01142a041
10.1002/ange.201608345
10.1002/1521-3765(20020703)8:13<2955::AID-CHEM2955>3.0.CO;2-Q
10.1002/ange.201812167
10.1002/ange.201707702
10.1039/C9SC00595A
10.1021/ja01617a025
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References Irrgang, T (WOS:000460199900006) 2019; 119
Talwar, D (WOS:000354190800046) 2015; 54
Scheeren, C (WOS:000247436400014) 2007; 26
Wang, Z. (000859341300001.8) 2019; 131
Qiu, ZH (WOS:000468818700002) 2019; 10
Nam, TG (WOS:000248896400047) 2007; 129
Shao, ZH (WOS:000388252700027) 2016; 55
Ogo, S (WOS:000172243200022) 2001; 20
Brasse, M (WOS:000289523000049) 2011; 47
Wu, JJ (WOS:000320776900034) 2013; 52
Rösler, S (WOS:000368057400006) 2015; 54
Tan, ZD (WOS:000528359400035) 2020; 23
Qiu, ZH (WOS:000411730500027) 2017; 8
He, QL (WOS:000726292000001) 2022; 364
Wang, JB (WOS:000188963600045) 2004; 14
Chen, X. (000859341300001.30) 2017; 129
Xu, XC (WOS:000704418200017) 2021; 402
Samec, JSM (WOS:000176724800016) 2002; 8
BENKESER, RA (WOS:A1955WB85900025) 1955; 77
Brewster, TP (WOS:000326487800015) 2013; 135
Liang, WY (WOS:000589942900022) 2020; 22
Chatterjee, I (WOS:000349209200056) 2015; 54
Bai, XG (WOS:000547468700030) 2020; 22
Tan, ZD (WOS:000598540500016) 2020; 392
Soetens, M (WOS:000397879500006) 2017; 9
BENKESER, RA (WOS:A1952UB43300041) 1952; 74
He, W (WOS:000337869800019) 2014; 16
Chen, XW (WOS:000508468900020) 2020; 85
Ai, WY (WOS:000460199900011) 2019; 119
Chen, XZ (WOS:000704418200016) 2021; 402
ref9/cit9
ref17/cit17b
ref6/cit6
ref3/cit3
ref1/cit1d
ref17/cit17a
ref11/cit11
ref16/cit16
ref8/cit8a
ref10/cit10a
ref10/cit10b
ref8/cit8b
ref12/cit12b
ref12/cit12a
ref14/cit14
ref2/cit2b
ref5/cit5
ref2/cit2a
ref1/cit1a
ref1/cit1c
ref1/cit1b
ref4/cit4a
ref4/cit4b
ref4/cit4c
ref7/cit7f
ref7/cit7e
ref7/cit7d
ref15/cit15
ref13/cit13
ref7/cit7c
ref7/cit7b
ref7/cit7a
References_xml – volume: 135
  start-page: 16022
  year: 2013
  ident: WOS:000326487800015
  article-title: Hydrogenation of Carboxylic Acids Catalyzed by Half-Sandwich Complexes of Iridium and Rhodium
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/ja408149n
  contributor:
    fullname: Brewster, TP
– volume: 54
  start-page: 15046
  year: 2015
  ident: WOS:000368057400006
  article-title: Cobalt-Catalyzed Alkylation of Aromatic Amines by Alcohols
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.201507955
  contributor:
    fullname: Rösler, S
– volume: 10
  start-page: 4775
  year: 2019
  ident: WOS:000468818700002
  article-title: Direct conversion of phenols into primary anilines with hydrazine catalyzed by palladium
  publication-title: CHEMICAL SCIENCE
  doi: 10.1039/c9sc00595a
  contributor:
    fullname: Qiu, ZH
– volume: 392
  start-page: 135
  year: 2020
  ident: WOS:000598540500016
  article-title: Selective reductive cross-coupling of N-heteroarenes by an unsymmetrical PNP-ligated manganese catalyst
  publication-title: JOURNAL OF CATALYSIS
  doi: 10.1016/j.jcat.2020.09.036
  contributor:
    fullname: Tan, ZD
– volume: 22
  start-page: 8291
  year: 2020
  ident: WOS:000589942900022
  article-title: Mono/Dual Amination of Phenols with Amines in Water
  publication-title: ORGANIC LETTERS
  doi: 10.1021/acs.orglett.0c02924
  contributor:
    fullname: Liang, WY
– volume: 52
  start-page: 6983
  year: 2013
  ident: WOS:000320776900034
  article-title: Acceptorless Dehydrogenation of Nitrogen Heterocycles with a Versatile Iridium Catalyst
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.201300292
  contributor:
    fullname: Wu, JJ
– volume: 131
  start-page: 260
  year: 2019
  ident: 000859341300001.8
  article-title: Multicomponent Reactions of Pyridines To Give Ring -Fused Pyridiniums: In Situ Activation Strategy Using 1,2-Dichloroethane as a Vinyl Equivalent
  publication-title: Angew. Chem
  contributor:
    fullname: Wang, Z.
– volume: 55
  start-page: 14653
  year: 2016
  ident: WOS:000388252700027
  article-title: Mild and Selective Cobalt-Catalyzed Chemodivergent Transfer Hydrogenation of Nitriles
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.201608345
  contributor:
    fullname: Shao, ZH
– volume: 9
  start-page: 929
  year: 2017
  ident: WOS:000397879500006
  article-title: (η5-Pentamethylcyclopentadienyl)iridium Complex Catalyzed Imine Reductions Utilizing the Biomimetic 1,4-NAD(P)H Cofactor and N-Benzyl-1,4-dihydronicotinamide as the Hydride-Transfer Agent
  publication-title: CHEMCATCHEM
  doi: 10.1002/cctc.201601307
  contributor:
    fullname: Soetens, M
– volume: 129
  start-page: 10211
  year: 2007
  ident: WOS:000248896400047
  article-title: Tetrahydro-1,8-naphthyridinol analogues of α-tocopherol as antioxidants in lipid membranes and low-density lipoproteins
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/ja072371m
  contributor:
    fullname: Nam, TG
– volume: 119
  start-page: 2524
  year: 2019
  ident: WOS:000460199900006
  article-title: 3d-Metal Catalyzed N- and C-Alkylation Reactions via Borrowing Hydrogen or Hydrogen Autotransfer
  publication-title: CHEMICAL REVIEWS
  doi: 10.1021/acs.chemrev.8b00306
  contributor:
    fullname: Irrgang, T
– volume: 47
  start-page: 5019
  year: 2011
  ident: WOS:000289523000049
  article-title: A facile, metal- and solvent-free, autoxidative coupling of quinolines with indoles and pyrroles
  publication-title: CHEMICAL COMMUNICATIONS
  doi: 10.1039/c1cc10507h
  contributor:
    fullname: Brasse, M
– volume: 129
  start-page: 14420
  year: 2017
  ident: 000859341300001.30
  article-title: Hydrogen Transfer -Mediated a-Functionalization of 1,8-Naphthyridines by a Strategy Overcoming the Over -Hydrogenation Barrier
  publication-title: Angew. Chem
  contributor:
    fullname: Chen, X.
– volume: 8
  start-page: 6954
  year: 2017
  ident: WOS:000411730500027
  article-title: Formal aromaticity transfer for palladiumcatalyzed coupling between phenols and pyrrolidines/indolines
  publication-title: CHEMICAL SCIENCE
  doi: 10.1039/c7sc02578e
  contributor:
    fullname: Qiu, ZH
– volume: 74
  start-page: 5699
  year: 1952
  ident: WOS:A1952UB43300041
  article-title: THE TRUE IDENTITY OF THE SOLVATED FREE RADICAL TRIPHENYLSILICYL ETHYLAMMINE - THE MULTIPLE ADDITION OF LITHIUM TO AN AROMATIC SYSTEM IN ETHYLAMINE
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  contributor:
    fullname: BENKESER, RA
– volume: 54
  start-page: 5223
  year: 2015
  ident: WOS:000354190800046
  article-title: Regioselective Acceptorless Dehydrogenative Coupling of N-Heterocycles toward Functionalized Quinolines, Phenanthrolines, and Indoles
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.201500346
  contributor:
    fullname: Talwar, D
– volume: 14
  start-page: 1049
  year: 2004
  ident: WOS:000188963600045
  article-title: Non-peptide αvβ3 antagonists.: Part 7:: 3-Substituted tetrahydro-[1,8]naphthyridine derivatives
  publication-title: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
  doi: 10.1016/j.bmcl.2003.11.036
  contributor:
    fullname: Wang, JB
– volume: 54
  start-page: 1965
  year: 2015
  ident: WOS:000349209200056
  article-title: B(C6F5)3-Catalyzed Transfer Hydrogenation of Imines and Related Heteroarenes Using Cyclohexa-1,4-dienes as a Dihydrogen Source
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.201409246
  contributor:
    fullname: Chatterjee, I
– volume: 364
  start-page: 459
  year: 2022
  ident: WOS:000726292000001
  article-title: Site-Selective 1,4-Difunctionalization of Nitrogen Heteroaromatics for Constructing Vinylidene Heterocycles
  publication-title: ADVANCED SYNTHESIS & CATALYSIS
  doi: 10.1002/adsc.202101098
  contributor:
    fullname: He, QL
– volume: 119
  start-page: 2876
  year: 2019
  ident: WOS:000460199900011
  article-title: Hydride Transfer Reactions Catalyzed by Cobalt Complexes
  publication-title: CHEMICAL REVIEWS
  doi: 10.1021/acs.chemrev.8b00404
  contributor:
    fullname: Ai, WY
– volume: 402
  start-page: 325
  year: 2021
  ident: WOS:000704418200016
  article-title: Cp*Ir complex bearing a flexible bridging and functional 2,2′- methylenebibenzimidazole ligand as an auto-tandem catalyst for the synthesis of N-methyl tertiary amines from imines via transfer hydrogenation/N-methylation with methanol
  publication-title: JOURNAL OF CATALYSIS
  doi: 10.1016/j.jcat.2021.08.037
  contributor:
    fullname: Chen, XZ
– volume: 8
  start-page: 2955
  year: 2002
  ident: WOS:000176724800016
  article-title: Ruthenium-catalyzed transfer hydrogenation of imines by propan-2-ol in benzene
  publication-title: CHEMISTRY-A EUROPEAN JOURNAL
  contributor:
    fullname: Samec, JSM
– volume: 77
  start-page: 3230
  year: 1955
  ident: WOS:A1955WB85900025
  article-title: REDUCTION OF ORGANIC COMPOUNDS BY LITHIUM IN LOW MOLECULAR WEIGHT AMINES .1. SELECTIVE REDUCTION OF AROMATIC HYDROCARBONS TO MONOOLEFINS
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  contributor:
    fullname: BENKESER, RA
– volume: 85
  start-page: 508
  year: 2020
  ident: WOS:000508468900020
  article-title: Hydrogen-Transfer-Mediated N-Arylation of Naphthols Using Indolines as Hydrogen Donors
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  doi: 10.1021/acs.joc.9b02558
  contributor:
    fullname: Chen, XW
– volume: 402
  start-page: 335
  year: 2021
  ident: WOS:000704418200017
  article-title: From selective transfer hydrogenation to selective hydrogen auto-transfer process: An efficient method for the synthesis of alkenyl ketones via iridium-catalyzed α-alkylation of ketones with alkenyl alcohols
  publication-title: JOURNAL OF CATALYSIS
  doi: 10.1016/j.jcat.2021.08.038
  contributor:
    fullname: Xu, XC
– volume: 20
  start-page: 4903
  year: 2001
  ident: WOS:000172243200022
  article-title: pH-dependent transfer hydrogenation, reductive amination, and dehalogenation of water-soluble carbonyl compounds and alkyl halides promoted by Cp*Ir complexes
  publication-title: ORGANOMETALLICS
  doi: 10.1021/om010523v
  contributor:
    fullname: Ogo, S
– volume: 26
  start-page: 3336
  year: 2007
  ident: WOS:000247436400014
  article-title: Stereoselective "electrophilic" cyclometalation of planar-prochiral (η6-arene)tricarbonylchromium complexes with asymmetric metal centers: pseudo-T-4 [Cp*RhCl2]2 and [Cp*IrCl2]2
  publication-title: ORGANOMETALLICS
  doi: 10.1021/om070170l
  contributor:
    fullname: Scheeren, C
– volume: 22
  start-page: 5068
  year: 2020
  ident: WOS:000547468700030
  article-title: Regioselective and Diastereoselective Dearomative Multifunctionalization of In-Situ-Activated Azaarenes: An Access to Bridged Azaheterocycles
  publication-title: ORGANIC LETTERS
  doi: 10.1021/acs.orglett.0c01648
  contributor:
    fullname: Bai, XG
– volume: 23
  start-page: ARTN 101003
  year: 2020
  ident: WOS:000528359400035
  article-title: Hydrogen Transfer-Mediated Multicomponent Reaction for Direct Synthesis of Quinazolines by a Naphthyridine-Based Iridium Catalyst
  publication-title: ISCIENCE
  doi: 10.1016/j.isci.2020.101003
  contributor:
    fullname: Tan, ZD
– volume: 16
  start-page: 3244
  year: 2014
  ident: WOS:000337869800019
  article-title: Halogen-Bonding-induced Hydrogen Transfer to C=N Bond with Hantzsch Ester
  publication-title: ORGANIC LETTERS
  doi: 10.1021/ol501259q
  contributor:
    fullname: He, W
– ident: ref7/cit7d
  doi: 10.1021/acs.chemrev.8b00306
– ident: ref3/cit3
  doi: 10.1039/c1cc10507h
– ident: ref4/cit4c
  doi: 10.1021/acs.orglett.0c01648
– ident: ref15/cit15
  doi: 10.1021/om010523v
– ident: ref16/cit16
  doi: 10.1002/cctc.201601307
– ident: ref9/cit9
  doi: 10.1016/j.isci.2020.101003
– ident: ref7/cit7f
  doi: 10.1039/C7SC02578E
– ident: ref10/cit10a
  doi: 10.1002/ange.201500346
– ident: ref1/cit1d
  doi: 10.1021/ol501259q
– ident: ref10/cit10b
  doi: 10.1002/anie.201300292
– ident: ref17/cit17b
  doi: 10.1016/j.jcat.2020.09.036
– ident: ref2/cit2a
  doi: 10.1021/ja01142a041
– ident: ref1/cit1a
  doi: 10.1016/j.bmcl.2003.11.036
– ident: ref12/cit12b
  doi: 10.1002/anie.201300292
– ident: ref11/cit11
  doi: 10.1021/acs.orglett.0c02924
– ident: ref8/cit8a
  doi: 10.1016/j.jcat.2021.08.037
– ident: ref14/cit14
  doi: 10.1021/ja408149n
– ident: ref7/cit7c
  doi: 10.1021/acs.chemrev.8b00404
– ident: ref7/cit7b
  doi: 10.1002/ange.201608345
– ident: ref8/cit8b
  doi: 10.1016/j.jcat.2021.08.038
– ident: ref12/cit12a
  doi: 10.1002/1521-3765(20020703)8:13<2955::AID-CHEM2955>3.0.CO;2-Q
– ident: ref4/cit4a
  doi: 10.1002/ange.201812167
– ident: ref7/cit7a
  doi: 10.1002/anie.201507955
– ident: ref1/cit1b
  doi: 10.1021/ja072371m
– ident: ref4/cit4b
  doi: 10.1002/adsc.202101098
– ident: ref1/cit1c
  doi: 10.1002/anie.201409246
– ident: ref17/cit17a
  doi: 10.1002/ange.201707702
– ident: ref13/cit13
  doi: 10.1021/om070170l
– ident: ref7/cit7e
  doi: 10.1039/C9SC00595A
– ident: ref2/cit2b
  doi: 10.1021/ja01617a025
– ident: ref5/cit5
  doi: 10.1016/j.jcat.2020.09.036
– ident: ref6/cit6
  doi: 10.1021/acs.joc.9b02558
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Snippet An iridium-catalyzed hydrogen transfer strategy, enabling straightforward access to tetrahydropyridine derivatives from aryl-1,8-naphthyridines and indolines...
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SubjectTerms Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Title Hydrogen Transfer Coupling with 100% Atom Economy: Synthesis of 2‑Indolyltetrahydronaphthyridine Derivatives
URI http://dx.doi.org/10.1021/acs.joc.2c01436
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