/ Home
/ SUBMISSION

/ The BJOC
/ Diamond Open Access
/ Journal Statistics
/ Editorial Board
/ Community
/ Call for papers

/ Latest Articles
/ Most accessed
/ Thematic issues
/ Volumes
/ Authors

/ Alerts

/ TWITTER
/ LINKEDIN
/ Mastodon
/ RSS FEED

Empty search

Article Type

Publication Date Range

Search Tips

This search combines search strings from the content search (i.e. "Full Text", "Author", "Title", "Abstract", or "Keywords") with "Article Type" and "Publication Date Range" using the AND operator.

Search Examples

aromatic	the word “aromatic”
aromatic aldehyde	the word “aromatic” OR “aldehyde”
+aromatic +aldehyde	both words “aromatic” AND “aldehyde”
+aromatic -aldehyde	the word “aromatic” but NOT “aldehyde”
“aromatic aldehyde”	the exact phrase “aromatic aldehyde”
benz*	words which begin with “benz”, such as “benzene” or “benzyl”
benz*yl	words that begin with “benz” and end with “yl”, such as “benzyl” or “benzoyl”
benzyl~	words that are close to the word “benzyl”, such as “benzoyl” (i.e., fuzzy search)

Search results

Search for "acyloin reaction" in Full Text gives 2 result(s) in Beilstein Journal of Organic Chemistry.

Correction: Recent advances in N-heterocyclic carbene (NHC)-catalysed benzoin reactions

Rajeev S. Menon,
Akkattu T. Biju and
Vijay Nair

Beilstein J. Org. Chem. 2016, 12, 2124–2124, doi:10.3762/bjoc.12.201

Interdisciplinary Science and Technology,Trivandrum 695 019, India.; Fax: +91 471 2491712; Tel: +91 471 2490406 10.3762/bjoc.12.201 Keywords: acyloin reaction; benzoin reaction; N-heterocyclic carbenes; organocatalysis; umpolung; On page 446, column 2, the sentence “Inoue and co-workers found that it promotes

PDF

Original
Article

Correction

Published 04 Oct 2016

Full text

Recent advances in N-heterocyclic carbene (NHC)-catalysed benzoin reactions

Rajeev S. Menon,
Akkattu T. Biju and
Vijay Nair

Beilstein J. Org. Chem. 2016, 12, 444–461, doi:10.3762/bjoc.12.47

the earliest known carbon–carbon bond-forming reactions catalysed by NHCs. The rapid growth of NHC catalysis in general has resulted in the development of a variety of benzoin and benzoin-type reactions. An overview of such NHC-catalysed benzoin reactions is presented. Keywords: acyloin reaction

PDF

Graphical Abstract

Scheme 1: Breslow’s proposal on the mechanism of the benzoin condensation.

Jump to Scheme 1

Scheme 2: Imidazolium carbene-catalysed homo-benzoin condensation.

Jump to Scheme 2

Scheme 3: Homo-benzoin condensation in aqueous medium.

Jump to Scheme 3

Scheme 4: Homobenzoin condensation catalysed by bis(benzimidazolium) salt 8.

Jump to Scheme 4

Scheme 5: List of assorted chiral NHC-catalysts used for asymmetric homobenzoin condensation.

Jump to Scheme 5

Scheme 6: A rigid bicyclic triazole precatalyst 15 in an efficient enantioselective benzoin reaction.

Jump to Scheme 6

Scheme 7: Inoue’s report of cross-benzoin reactions.

Jump to Scheme 7

Scheme 8: Cross-benzoin reactions catalysed by thiazolium salt 17.

Jump to Scheme 8

Scheme 9: Catalyst-controlled divergence in cross-benzoin reactions.

Jump to Scheme 9

Scheme 10: Chemoselective cross-benzoin reactions catalysed by a bulky NHC.

Jump to Scheme 10

Scheme 11: Selective intermolecular cross-benzoin condensation reactions of aromatic and aliphatic aldehydes.

Jump to Scheme 11

Scheme 12: Chemoselective cross-benzoin reaction of aliphatic and aromatic aldehydes.

Jump to Scheme 12

Scheme 13: Cross-benzoin reactions of trifluoromethyl ketones developed by Enders.

Jump to Scheme 13

Scheme 14: Cross-benzoin reactions of aldehydes and α-ketoesters.

Jump to Scheme 14

Scheme 15: Enantioselective cross-benzoin reactions of aliphatic aldehydes and α-ketoesters.

Jump to Scheme 15

Scheme 16: Dynamic kinetic resolution of β-halo-α-ketoesters via cross-benzoin reaction.

Jump to Scheme 16

Scheme 17: Enantioselective benzoin reaction of aldehydes and alkynones.

Jump to Scheme 17

Scheme 18: Aza-benzoin reaction of aldehydes and acylimines.

Jump to Scheme 18

Scheme 19: NHC-catalysed diastereoselective synthesis of cis-2-amino 3-hydroxyindanones.

Jump to Scheme 19

Scheme 20: Cross-aza-benzoin reactions of aldehydes with aromatic imines.

Jump to Scheme 20

Scheme 21: Enantioselective cross aza-benzoin reaction of aliphatic aldehydes with N-Boc-imines.

Jump to Scheme 21

Scheme 22: Chemoselective cross aza-benzoin reaction of aldehydes with N-PMP-imino esters.

Jump to Scheme 22

Scheme 23: NHC-catalysed coupling reaction of acylsilanes with imines.

Jump to Scheme 23

Scheme 24: Thiazolium salt-mediated enantioselective cross-aza-benzoin reaction.

Jump to Scheme 24

Scheme 25: Aza-benzoin reaction of enals with activated ketimines.

Jump to Scheme 25

Scheme 26: Isatin derived ketimines as electrophiles in cross aza-benzoin reaction with enals.

Jump to Scheme 26

Scheme 27: Aza-benzoin reaction of aldehydes and phosphinoylimines catalysed by the BAC-carbene.

Jump to Scheme 27

Scheme 28: Nitrosoarenes as the electrophilic component in benzoin-initiated cascade reaction.

Jump to Scheme 28

Scheme 29: One-pot synthesis of hydroxamic esters via aza-benzoin reaction.

Jump to Scheme 29

Scheme 30: Cookson and Lane’s report of intramolecular benzoin condensation.

Jump to Scheme 30

Scheme 31: Intramolecular cross-benzoin condensation between aldehyde and ketone moieties.

Jump to Scheme 31

Scheme 32: Intramolecular crossed aldehyde-ketone benzoin reactions.

Jump to Scheme 32

Scheme 33: Enantioselective intramolecular crossed aldehyde-ketone benzoin reaction.

Jump to Scheme 33

Scheme 34: Chromanone synthesis via enantioselective intramolecular cross-benzoin reaction.

Jump to Scheme 34

Scheme 35: Intramolecular cross-benzoin reaction of chalcones.

Jump to Scheme 35

Scheme 36: Synthesis of bicyclic tertiary alcohols by intramolecular benzoin reaction.

Jump to Scheme 36

Scheme 37: A multicatalytic Michael–benzoin cascade process for cyclopentanone synthesis.

Jump to Scheme 37

Scheme 38: Enamine-NHC dual-catalytic, Michael–benzoin cascade reaction.

Jump to Scheme 38

Scheme 39: Iminium-cross-benzoin cascade reaction of enals and β-oxo sulfones.

Jump to Scheme 39

Scheme 40: Intramolecular benzoin condensation of carbohydrate-derived dialdehydes.

Jump to Scheme 40

Scheme 41: Enantioselective intramolecular benzoin reactions of N-tethered keto-aldehydes.

Jump to Scheme 41

Scheme 42: Asymmetric cross-benzoin reactions promoted by camphor-derived catalysts.

Jump to Scheme 42

Scheme 43: NHC-Brønsted base co-catalysis in a benzoin–Michael–Michael cascade.

Jump to Scheme 43

Scheme 44: Divergent catalytic dimerization of 2-formylcinnamates.

Jump to Scheme 44

Scheme 45: One-pot, multicatalytic asymmetric synthesis of tetrahydrocarbazole derivatives.

Jump to Scheme 45

Scheme 46: NHC-chiral secondary amine co-catalysis for the synthesis of complex spirocyclic scaffolds.

Jump to Scheme 46

Album

Correction

Review

Published 09 Mar 2016

Full text

Other Beilstein-Institut Open Science Activities

/ Help / Support & Contact / Alerts / Privacy Policy / Terms & Conditions / Impressum