Chemical Reviews, volume 121, issue 1, pages 412-484
Decarboxylative Halogenation of Organic Compounds
Publication type: Journal Article
Publication date: 2020-11-17
Journal:
Chemical Reviews
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 62.1
ISSN: 00092665, 15206890
General Chemistry
Abstract
Decarboxylative halogenation, or halodecarboxylation, represents one of the fundamental key methods for the synthesis of ubiquitous organic halides. The method is based on conversion of carboxylic acids to the corresponding organic halides via selective cleavage of a carbon-carbon bond between the skeleton of the molecule and the carboxylic group and the liberation of carbon dioxide. In this review, we discuss and analyze major approaches for the conversion of alkanoic, alkenoic, acetylenic, and (hetero)aromatic acids to the corresponding alkyl, alkenyl, alkynyl, and (hetero)aryl halides. These methods include the preparation of families of valuable organic iodides, bromides, chlorides, and fluorides. The historic and modern methods for halodecarboxylation reactions are broadly discussed, including analysis of their advantages and drawbacks. We critically address the features, reaction selectivity, substrate scopes, and limitations of the approaches. In the available cases, mechanistic details of the reactions are presented, and the generality and uniqueness of the different mechanistic pathways are highlighted. The challenges, opportunities, and future directions in the field of decarboxylative halogenation are provided.
Top-30
Citations by journals
|
2
4
6
8
10
12
14
16
18
|
|
|
Organic Chemistry Frontiers
17 publications, 11.49%
|
|
|
Organic Letters
17 publications, 11.49%
|
|
|
Journal of the American Chemical Society
10 publications, 6.76%
|
|
|
Angewandte Chemie - International Edition
7 publications, 4.73%
|
|
|
Angewandte Chemie
7 publications, 4.73%
|
|
|
Journal of Organic Chemistry
7 publications, 4.73%
|
|
|
Organic and Biomolecular Chemistry
7 publications, 4.73%
|
|
|
Chemical Science
5 publications, 3.38%
|
|
|
Chemical Communications
5 publications, 3.38%
|
|
|
ACS Catalysis
4 publications, 2.7%
|
|
|
Green Chemistry
4 publications, 2.7%
|
|
|
Molecules
3 publications, 2.03%
|
|
|
Advanced Synthesis and Catalysis
3 publications, 2.03%
|
|
|
Chemical Research in Chinese Universities
2 publications, 1.35%
|
|
|
Tetrahedron Letters
2 publications, 1.35%
|
|
|
Chemical Engineering Journal
2 publications, 1.35%
|
|
|
Chemistry - A European Journal
2 publications, 1.35%
|
|
|
European Journal of Organic Chemistry
2 publications, 1.35%
|
|
|
Synthesis
2 publications, 1.35%
|
|
|
ACS Sustainable Chemistry and Engineering
2 publications, 1.35%
|
|
|
RSC Advances
2 publications, 1.35%
|
|
|
Russian Chemical Reviews
2 publications, 1.35%
|
|
|
Beilstein Journal of Organic Chemistry
1 publication, 0.68%
|
|
|
Polymers
1 publication, 0.68%
|
|
|
Symmetry
1 publication, 0.68%
|
|
|
Frontiers in Chemistry
1 publication, 0.68%
|
|
|
Nature Chemistry
1 publication, 0.68%
|
|
|
Environmental Chemistry Letters
1 publication, 0.68%
|
|
|
Transactions of Tianjin University
1 publication, 0.68%
|
|
|
Journal of the Taiwan Institute of Chemical Engineers
1 publication, 0.68%
|
|
|
2
4
6
8
10
12
14
16
18
|
Citations by publishers
|
5
10
15
20
25
30
35
40
45
|
|
|
American Chemical Society (ACS)
42 publications, 28.38%
|
|
|
Royal Society of Chemistry (RSC)
40 publications, 27.03%
|
|
|
Wiley
30 publications, 20.27%
|
|
|
Elsevier
13 publications, 8.78%
|
|
|
Springer Nature
6 publications, 4.05%
|
|
|
Multidisciplinary Digital Publishing Institute (MDPI)
5 publications, 3.38%
|
|
|
Thieme
3 publications, 2.03%
|
|
|
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
2 publications, 1.35%
|
|
|
Beilstein-Institut
1 publication, 0.68%
|
|
|
Frontiers Media S.A.
1 publication, 0.68%
|
|
|
Tianjin Daxue/Tianjin University
1 publication, 0.68%
|
|
|
Taiwan Institute of Chemical Engineers
1 publication, 0.68%
|
|
|
Asian Journal of Chemistry
1 publication, 0.68%
|
|
|
Taylor & Francis
1 publication, 0.68%
|
|
|
5
10
15
20
25
30
35
40
45
|
- 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":[24,40,48,36],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":["16.22","27.03","32.43","24.32"],"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":["Organic Chemistry Frontiers","Organic Letters","Journal of the American Chemical Society","Angewandte Chemie - International Edition","Angewandte Chemie","Journal of Organic Chemistry","Organic and Biomolecular Chemistry","Chemical Science","Chemical Communications","ACS Catalysis","Green Chemistry","Molecules","Advanced Synthesis and Catalysis","Chemical Research in Chinese Universities","Tetrahedron Letters","Chemical Engineering Journal","Chemistry - A European Journal","European Journal of Organic Chemistry","Synthesis","ACS Sustainable Chemistry and Engineering","RSC Advances","Russian Chemical Reviews","Beilstein Journal of Organic Chemistry","Polymers","Symmetry","Frontiers in Chemistry","Nature Chemistry","Environmental Chemistry Letters","Transactions of Tianjin University","Journal of the Taiwan Institute of Chemical Engineers"],"ids":[3991,3315,4813,19215,25450,8697,541,9646,9073,4873,1017,1770,3906,1401,6133,16275,24708,19472,10934,18886,3100,23802,21928,11204,21974,6407,17228,8849,3916,19382],"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\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/xqixcltwJYe6H8Uco2JbAFfIOzt7UNKH0OcPOPzO_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp","\/storage\/images\/resized\/ex6KJoZujZOZFZh7jGfeHauiftuB3CI7iwJVFRDg_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/4QWA67eqfcfyOiA8Wk7YnqroHFqQbTsmDJUYTCTg_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","",""],"datasets":[{"label":"","data":[17,17,10,7,7,7,7,5,5,4,4,3,3,2,2,2,2,2,2,2,2,2,1,1,1,1,1,1,1,1],"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":[11.49,11.49,6.76,4.73,4.73,4.73,4.73,3.38,3.38,2.7,2.7,2.03,2.03,1.35,1.35,1.35,1.35,1.35,1.35,1.35,1.35,1.35,0.68,0.68,0.68,0.68,0.68,0.68,0.68,0.68],"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":["American Chemical Society (ACS)","Royal Society of Chemistry (RSC)","Wiley","Elsevier","Springer Nature","Multidisciplinary Digital Publishing Institute (MDPI)","Thieme","Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii","Beilstein-Institut","Frontiers Media S.A.","Tianjin Daxue\/Tianjin University","Taiwan Institute of Chemical Engineers","Asian Journal of Chemistry","Taylor & Francis"],"ids":[40,123,11,17,8,202,135,9422,6139,208,1423,5505,6264,18],"codes":[0,0,0,0,0,0,0,0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/xqixcltwJYe6H8Uco2JbAFfIOzt7UNKH0OcPOPzO_medium.webp","\/storage\/images\/resized\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp","\/storage\/images\/resized\/ex6KJoZujZOZFZh7jGfeHauiftuB3CI7iwJVFRDg_medium.webp","\/storage\/images\/resized\/4QWA67eqfcfyOiA8Wk7YnqroHFqQbTsmDJUYTCTg_medium.webp","","","\/storage\/images\/resized\/Vb3hw5ha3GXFySkcFIRq7hedUzMGRVNprYvOwnlQ_medium.webp","\/storage\/images\/resized\/5YZtvLvkPZuc2JHOaZsjCvGSHFCuC3drUwN3YAc5_medium.webp"],"datasets":[{"label":"","data":[42,40,30,13,6,5,3,2,1,1,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[28.38,27.03,20.27,8.78,4.05,3.38,2.03,1.35,0.68,0.68,0.68,0.68,0.68,0.68],"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":[0,1,0,0],"percentage":["0","0.68","0","0"]},{"label":"Q3","backgroundColor":"rgb(251, 163,83)","data":[0,2,1,2],"percentage":["0","1.35","0.68","1.35"]},{"label":"Q2","backgroundColor":"rgb(232, 213, 89)","data":[3,4,3,4],"percentage":["2.03","2.7","2.03","2.7"]},{"label":"Q1","backgroundColor":"rgb(164, 207, 99)","data":[21,33,43,30],"percentage":["14.19","22.3","29.05","20.27"]},{"label":"Quartile not defined","backgroundColor":"#E5E7EB","data":[0,0,1,0],"percentage":["0","0","0.68","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":[1,4,1,3],"percentage":["0.68","2.7","0.68","2.03"]},{"label":"Q2","backgroundColor":"rgb(232, 213, 89)","data":[4,12,14,4],"percentage":["2.7","8.11","9.46","2.7"]},{"label":"Q1","backgroundColor":"rgb(164, 207, 99)","data":[15,21,31,27],"percentage":["10.14","14.19","20.95","18.24"]},{"label":"Quartile not defined","backgroundColor":"#E5E7EB","data":[4,3,2,2],"percentage":["2.7","2.03","1.35","1.35"]}]},"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 |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
Varenikov A., Shapiro E., Gandelman M. Decarboxylative Halogenation of Organic Compounds // Chemical Reviews. 2020. Vol. 121. No. 1. pp. 412-484.
GOST all authors (up to 50)
Copy
Varenikov A., Shapiro E., Gandelman M. Decarboxylative Halogenation of Organic Compounds // Chemical Reviews. 2020. Vol. 121. No. 1. pp. 412-484.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.chemrev.0c00813
UR - https://doi.org/10.1021/acs.chemrev.0c00813
TI - Decarboxylative Halogenation of Organic Compounds
T2 - Chemical Reviews
AU - Shapiro, Evgeny
AU - Varenikov, Andrii
AU - Gandelman, Mark
PY - 2020
DA - 2020/11/17 00:00:00
PB - American Chemical Society (ACS)
SP - 412-484
IS - 1
VL - 121
SN - 0009-2665
SN - 1520-6890
ER -
Cite this
BibTex
Copy
@article{2020_Varenikov,
author = {Evgeny Shapiro and Andrii Varenikov and Mark Gandelman},
title = {Decarboxylative Halogenation of Organic Compounds},
journal = {Chemical Reviews},
year = {2020},
volume = {121},
publisher = {American Chemical Society (ACS)},
month = {nov},
url = {https://doi.org/10.1021/acs.chemrev.0c00813},
number = {1},
pages = {412--484},
doi = {10.1021/acs.chemrev.0c00813}
}
Cite this
MLA
Copy
Varenikov, Andrii, et al. “Decarboxylative Halogenation of Organic Compounds.” Chemical Reviews, vol. 121, no. 1, Nov. 2020, pp. 412-484. https://doi.org/10.1021/acs.chemrev.0c00813.