Organic Letters, volume 23, issue 9, pages 3320-3325

Nickel-Catalyzed Guerbet Type Reaction: C-Alkylation of Secondary Alcohols via Double (de)Hydrogenation

Reshma Babu ¹

Murugan Subaramanian ¹

Siba P Midya ¹

Ekambaram Balaraman ¹

Hide authors affiliations Show authors affiliations: 1 affiliation

Department of Chemistry, Indian Institute of Science Education and Research (IISER) Tirupati, Tirupati 517507, India |

Publication type: Journal Article

Publication date: 2021-04-21

American Chemical Society (ACS)

Journal: Organic Letters

Quartile SCImago

Quartile WOS

Impact factor: 5.2

ISSN: 15237060, 15237052

DOI: 10.1021/acs.orglett.1c00782

Copy DOI

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Abstract

Acceptorless double dehydrogenative cross-coupling of secondary and primary alcohols under nickel catalysis is reported. This Guerbet type reaction provides an atom- and a step-economical method for the C-alkylation of secondary alcohols under mild, benign conditions. A broad range of substrates including aromatic, cyclic, acyclic, and aliphatic alcohols was well tolerated. Interestingly, the C-alkylation of cholesterol derivatives and the double C-alkylation of cyclopentanol with various alcohols were also demonstrated.

By date By citations

Top-30

Citations by journals

	1 2 3 4
Organometallics	Organometallics, 4, 7.69% Organometallics 4 publications, 7.69%
Journal of Organic Chemistry	Journal of Organic Chemistry, 3, 5.77% Journal of Organic Chemistry 3 publications, 5.77%
Catalysis Science and Technology	Catalysis Science and Technology, 3, 5.77% Catalysis Science and Technology 3 publications, 5.77%
Organic and Biomolecular Chemistry	Organic and Biomolecular Chemistry, 3, 5.77% Organic and Biomolecular Chemistry 3 publications, 5.77%
ChemCatChem	ChemCatChem, 3, 5.77% ChemCatChem 3 publications, 5.77%
ACS Catalysis	ACS Catalysis, 3, 5.77% ACS Catalysis 3 publications, 5.77%
Chemical Communications	Chemical Communications, 3, 5.77% Chemical Communications 3 publications, 5.77%
Chemistry - An Asian Journal	Chemistry - An Asian Journal, 2, 3.85% Chemistry - An Asian Journal 2 publications, 3.85%
Angewandte Chemie	Angewandte Chemie, 2, 3.85% Angewandte Chemie 2 publications, 3.85%
Angewandte Chemie - International Edition	Angewandte Chemie - International Edition, 2, 3.85% Angewandte Chemie - International Edition 2 publications, 3.85%
Organic Letters	Organic Letters, 2, 3.85% Organic Letters 2 publications, 3.85%
Polymers	Polymers, 1, 1.92% Polymers 1 publication, 1.92%
Molecules	Molecules, 1, 1.92% Molecules 1 publication, 1.92%
Green Synthesis and Catalysis	Green Synthesis and Catalysis, 1, 1.92% Green Synthesis and Catalysis 1 publication, 1.92%
Journal of Catalysis	Journal of Catalysis, 1, 1.92% Journal of Catalysis 1 publication, 1.92%
Tetrahedron Letters	Tetrahedron Letters, 1, 1.92% Tetrahedron Letters 1 publication, 1.92%
Fuel	Fuel, 1, 1.92% Fuel 1 publication, 1.92%
Synlett	Synlett, 1, 1.92% Synlett 1 publication, 1.92%
Tetrahedron	Tetrahedron, 1, 1.92% Tetrahedron 1 publication, 1.92%
Chemical Record	Chemical Record, 1, 1.92% Chemical Record 1 publication, 1.92%
Advanced Synthesis and Catalysis	Advanced Synthesis and Catalysis, 1, 1.92% Advanced Synthesis and Catalysis 1 publication, 1.92%
Organic Chemistry Frontiers	Organic Chemistry Frontiers, 1, 1.92% Organic Chemistry Frontiers 1 publication, 1.92%
Optics Letters	Optics Letters, 1, 1.92% Optics Letters 1 publication, 1.92%
Chemical Science	Chemical Science, 1, 1.92% Chemical Science 1 publication, 1.92%
Synthetic Communications	Synthetic Communications, 1, 1.92% Synthetic Communications 1 publication, 1.92%
Topics in Organometallic Chemistry	Topics in Organometallic Chemistry, 1, 1.92% Topics in Organometallic Chemistry 1 publication, 1.92%
Journal of Chemical Sciences	Journal of Chemical Sciences, 1, 1.92% Journal of Chemical Sciences 1 publication, 1.92%
Journal of Molecular Structure	Journal of Molecular Structure, 1, 1.92% Journal of Molecular Structure 1 publication, 1.92%
Chemical Reviews	Chemical Reviews, 1, 1.92% Chemical Reviews 1 publication, 1.92%
ChemistrySelect	ChemistrySelect, 1, 1.92% ChemistrySelect 1 publication, 1.92%
	1 2 3 4

Citations by publishers

	2 4 6 8 10 12 14
Wiley	Wiley, 14, 26.92% Wiley 14 publications, 26.92%
American Chemical Society (ACS)	American Chemical Society (ACS), 13, 25% American Chemical Society (ACS) 13 publications, 25%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 11, 21.15% Royal Society of Chemistry (RSC) 11 publications, 21.15%
Elsevier	Elsevier, 6, 11.54% Elsevier 6 publications, 11.54%
Multidisciplinary Digital Publishing Institute (MDPI)	Multidisciplinary Digital Publishing Institute (MDPI), 2, 3.85% Multidisciplinary Digital Publishing Institute (MDPI) 2 publications, 3.85%
Springer Nature	Springer Nature, 2, 3.85% Springer Nature 2 publications, 3.85%
Thieme	Thieme, 1, 1.92% Thieme 1 publication, 1.92%
Optical Society of America	Optical Society of America, 1, 1.92% Optical Society of America 1 publication, 1.92%
Taylor & Francis	Taylor & Francis, 1, 1.92% Taylor & Francis 1 publication, 1.92%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii	Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii, 1, 1.92% Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii 1 publication, 1.92%
	2 4 6 8 10 12 14

We do not take into account publications without a DOI.
Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
Statistics recalculated weekly.

{"yearsCitations":{"type":"bar","data":{"show":true,"labels":[2021,2022,2023,2024],"ids":[0,0,0,0],"codes":[0,0,0,0],"imageUrls":["","","",""],"datasets":[{"label":"Citations number","data":[8,14,17,13],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":["15.38","26.92","32.69","25"],"barThickness":null}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"journals":{"type":"bar","data":{"show":true,"labels":["Organometallics","Journal of Organic Chemistry","Catalysis Science and Technology","Organic and Biomolecular Chemistry","ChemCatChem","ACS Catalysis","Chemical Communications","Chemistry - An Asian Journal","Angewandte Chemie","Angewandte Chemie - International Edition","Organic Letters","Polymers","Molecules","Green Synthesis and Catalysis","Journal of Catalysis","Tetrahedron Letters","Fuel","Synlett","Tetrahedron","Chemical Record","Advanced Synthesis and Catalysis","Organic Chemistry Frontiers","Optics Letters","Chemical Science","Synthetic Communications","Topics in Organometallic Chemistry","Journal of Chemical Sciences","Journal of Molecular Structure","Chemical Reviews","ChemistrySelect"],"ids":[1409,8697,2605,541,10149,4873,9073,10120,25450,19215,3315,11204,1770,26555,20883,6133,23541,10217,3439,22413,3906,3991,854,9646,1646,23840,13500,9347,13718,8021],"codes":[0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/xqixcltwJYe6H8Uco2JbAFfIOzt7UNKH0OcPOPzO_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/bypZPcr6C4twKiQVCUCGc0GF4cH6aUWmpClD3hsH_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/5YZtvLvkPZuc2JHOaZsjCvGSHFCuC3drUwN3YAc5_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp"],"datasets":[{"label":"","data":[4,3,3,3,3,3,3,2,2,2,2,1,1,1,1,1,1,1,1,1,1,1,1,1,1,1,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[7.69,5.77,5.77,5.77,5.77,5.77,5.77,3.85,3.85,3.85,3.85,1.92,1.92,1.92,1.92,1.92,1.92,1.92,1.92,1.92,1.92,1.92,1.92,1.92,1.92,1.92,1.92,1.92,1.92,1.92],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Journals","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"publishers":{"type":"bar","data":{"show":true,"labels":["Wiley","American Chemical Society (ACS)","Royal Society of Chemistry (RSC)","Elsevier","Multidisciplinary Digital Publishing Institute (MDPI)","Springer Nature","Thieme","Optical Society of America","Taylor & Francis","Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii"],"ids":[11,40,123,17,202,8,135,375,18,9422],"codes":[0,0,0,0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/xqixcltwJYe6H8Uco2JbAFfIOzt7UNKH0OcPOPzO_medium.webp","\/storage\/images\/resized\/bypZPcr6C4twKiQVCUCGc0GF4cH6aUWmpClD3hsH_medium.webp","\/storage\/images\/resized\/5YZtvLvkPZuc2JHOaZsjCvGSHFCuC3drUwN3YAc5_medium.webp","\/storage\/images\/resized\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp"],"datasets":[{"label":"","data":[14,13,11,6,2,2,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[26.92,25,21.15,11.54,3.85,3.85,1.92,1.92,1.92,1.92],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Publishers","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"yearsCitationsQuartiles":{"type":"bar","data":{"show":true,"labels":[2021,2022,2023,2024],"ids":[],"codes":[],"imageUrls":[],"datasets":[{"label":"Q4","backgroundColor":"rgb(221,90,78)","data":[0,0,0,0],"percentage":["0","0","0","0"]},{"label":"Q3","backgroundColor":"rgb(251, 163,83)","data":[0,1,1,1],"percentage":["0","1.92","1.92","1.92"]},{"label":"Q2","backgroundColor":"rgb(232, 213, 89)","data":[1,3,1,4],"percentage":["1.92","5.77","1.92","7.69"]},{"label":"Q1","backgroundColor":"rgb(164, 207, 99)","data":[7,10,14,8],"percentage":["13.46","19.23","26.92","15.38"]},{"label":"Quartile not defined","backgroundColor":"#E5E7EB","data":[0,0,1,0],"percentage":["0","0","1.92","0"]}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":true},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":true}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations quartiles by SCImago per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"yearsCitationsQuartilesWs":{"type":"bar","data":{"show":true,"labels":[2021,2022,2023,2024],"ids":[],"codes":[],"imageUrls":[],"datasets":[{"label":"Q4","backgroundColor":"rgb(221,90,78)","data":[0,0,0,0],"percentage":["0","0","0","0"]},{"label":"Q3","backgroundColor":"rgb(251, 163,83)","data":[1,2,1,3],"percentage":["1.92","3.85","1.92","5.77"]},{"label":"Q2","backgroundColor":"rgb(232, 213, 89)","data":[4,6,6,6],"percentage":["7.69","11.54","11.54","11.54"]},{"label":"Q1","backgroundColor":"rgb(164, 207, 99)","data":[3,6,6,4],"percentage":["5.77","11.54","11.54","7.69"]},{"label":"Quartile not defined","backgroundColor":"#E5E7EB","data":[0,0,4,0],"percentage":["0","0","7.69","0"]}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":true},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":true}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations quartiles by WoS per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}}}

Are you a researcher?

Create a profile to get free access to personal recommendations for colleagues and new articles.

Metrics

Cite this

GOST |

Cite this

GOST Copy

Babu R. et al. Nickel-Catalyzed Guerbet Type Reaction: C-Alkylation of Secondary Alcohols via Double (de)Hydrogenation // Organic Letters. 2021. Vol. 23. No. 9. pp. 3320-3325.

GOST all authors (up to 50) Copy

Babu R., Subaramanian M., Midya S. P., Balaraman E. Nickel-Catalyzed Guerbet Type Reaction: C-Alkylation of Secondary Alcohols via Double (de)Hydrogenation // Organic Letters. 2021. Vol. 23. No. 9. pp. 3320-3325.

RIS |

Cite this

RIS Copy

TY - JOUR

DO - 10.1021/acs.orglett.1c00782

UR - https://doi.org/10.1021/acs.orglett.1c00782

TI - Nickel-Catalyzed Guerbet Type Reaction: C-Alkylation of Secondary Alcohols via Double (de)Hydrogenation

T2 - Organic Letters

AU - Babu, Reshma

AU - Midya, Siba P

AU - Balaraman, Ekambaram

AU - Subaramanian, Murugan

PY - 2021

DA - 2021/04/21 00:00:00

PB - American Chemical Society (ACS)

SP - 3320-3325

IS - 9

VL - 23

SN - 1523-7060

SN - 1523-7052

ER -

BibTex |

Cite this

BibTex Copy

@article{2021_Babu,

author = {Reshma Babu and Siba P Midya and Ekambaram Balaraman and Murugan Subaramanian},

title = {Nickel-Catalyzed Guerbet Type Reaction: C-Alkylation of Secondary Alcohols via Double (de)Hydrogenation},

journal = {Organic Letters},

year = {2021},

volume = {23},

publisher = {American Chemical Society (ACS)},

month = {apr},

url = {https://doi.org/10.1021/acs.orglett.1c00782},

number = {9},

pages = {3320--3325},

doi = {10.1021/acs.orglett.1c00782}

}

MLA

Cite this

MLA Copy

Babu, Reshma, et al. “Nickel-Catalyzed Guerbet Type Reaction: C-Alkylation of Secondary Alcohols via Double (de)Hydrogenation.” Organic Letters, vol. 23, no. 9, Apr. 2021, pp. 3320-3325. https://doi.org/10.1021/acs.orglett.1c00782.

Found error?

Publisher

American Chemical Society (ACS)

Journal

Organic Letters

Quartile SCImago

Quartile WOS

Impact factor

5.2

ISSN

15237060 (Print)
15237052 (Electronic)