Expedient access to unsymmetrical triarylmethanes through N-heterocyclic carbene catalysed 1,6-conjugate addition of 2-naphthols to para-quinone methides

RSC Advances ◽  
2016 ◽  
Vol 6 (81) ◽  
pp. 77111-77115 ◽  
Author(s):  
Panjab Arde ◽  
Ramasamy Vijaya Anand
Keyword(s):  
Conjugate Addition ◽  
Base Catalyst ◽  
Quinone Methides ◽  
Brønsted Base

A direct and atom-economical protocol for the synthesis of unsymmetrical triarylmethanes through 1,6-conjugate addition of 2-naphthols topara-quinone methides using N-heterocyclic carbene as a Brønsted base catalyst is described.

Exploring bis-(amino)cyclopropenylidene as a non-covalent Brønsted base catalyst in conjugate addition reactions

2018 ◽  
Vol 16 (3) ◽  
pp. 384-388 ◽  
Author(s):  
Gurdeep Singh ◽  
Prithwish Goswami ◽  
Ramasamy Vijaya Anand
Keyword(s):  
Conjugate Addition ◽  
Addition Reactions ◽  
Base Catalyst ◽  
Quinone Methides ◽  
Carbon Nucleophiles ◽  
Catalytic Application ◽  
Brønsted Base

The catalytic application of bis-(amino)cyclopropenylidene, as a non-covalent Brønsted base, in the 1,4- and 1,6-conjugate addition of carbon nucleophiles to enones andp-quinone methides, respectively, is described.

N-Heterocyclic carbene catalysed 1,6-hydrophosphonylation of p-quinone methides and fuchsones: an atom economical route to unsymmetrical diaryl- and triarylmethyl phosphonates

2016 ◽  
Vol 14 (24) ◽  
pp. 5550-5554 ◽  
Author(s):  
Panjab Arde ◽  
Ramasamy Vijaya Anand
Keyword(s):  
Direct Method ◽  
Base Catalyst ◽  
Quinone Methides ◽  
Brønsted Base ◽  
A Direct Method

A direct method for the synthesis of diaryl- and triarylmethyl phosphonates through 1,6-hydrophosphonylation ofp-quinone methides and fuchsones using NHC as a Brønsted base catalyst is described.

Organocatalytic Asymmetric Tandem Conjugate Addition–Protonation of Azlactones to N-Itaconimides

Synlett ◽  
2017 ◽  
Vol 28 (11) ◽  
pp. 1310-1314 ◽  
Author(s):  
Xiaowei Zhao ◽  
Zhiyong Jiang ◽  
Gao Zhang ◽  
Yanli Yin
Keyword(s):  
Tertiary Amine ◽  
Conjugate Addition ◽  
Base Catalyst ◽  
Asymmetric Reaction ◽  
Efficient Approach ◽  
Brønsted Base ◽  
Catalytic Asymmetric

An unprecedented catalytic asymmetric reaction between azlactones and N-itaconimides has been developed. In the presence of an l-tert-leucine-based urea–tertiary amine Brønsted base catalyst, the tandem conjugate addition–protonation products could be attained in moderate yields with excellent enantio- and diastereoselectivities (up to 99% ee and >20:1 dr). The method provides an efficient approach to access valuable chiral γ-tertiary amine substituted succinimides containing nonadjacent stereocenters.

Copper-catalyzed 1,6-conjugate addition of para-quinone methides with diborylmethane

2021 ◽  
Author(s):  
Xin Li ◽  
Guoliang Gao ◽  
Songtao He ◽  
Qiuling Song
Keyword(s):  
Catalytic System ◽  
Conjugate Addition ◽  
Quinone Methides ◽  
High Yields

Presented herein is the first 1,6-conjugate addition of diborylmethane, which is promoted by a simple and inexpensive copper catalytic system. This method features high yields, good selectivities and broad functional...

Organocatalytic cascade 1,6-conjugate addition/annulation/tautomerization of functionalized para-quinone methides: Access to chiral 2-amino-4-aryl-4H-chromenes

2018 ◽  
Vol 29 (8) ◽  
pp. 1273-1276 ◽  
Author(s):  
Cong Duan ◽  
Ling Ye ◽  
Wenqin Xu ◽  
Xinying Li ◽  
Feng Chen ◽  
...  
Keyword(s):  
Conjugate Addition ◽  
Quinone Methides

1,6-Conjugate-Addition-Induced [2 + 1] Annulation of para-Quinone Methides and Pyrazolones: Synthesis of Bis-Spiro Compounds with Contiguous Quaternary Spiro-Centers

2019 ◽  
Vol 21 (19) ◽  
pp. 7736-7740 ◽  
Author(s):  
Someshwar B. Kale ◽  
Popat K. Jori ◽  
Thanusha Thatikonda ◽  
Rajesh G. Gonnade ◽  
Utpal Das
Keyword(s):  
Conjugate Addition ◽  
Spiro Compounds ◽  
Quinone Methides

Diastereo- and Enantioselective 1,6-Conjugate Addition of 2-Azaarylacetamides to para-Quinone Methides

2019 ◽  
Vol 21 (15) ◽  
pp. 6063-6067 ◽  
Author(s):  
Yan Wang ◽  
Kaixuan Wang ◽  
Weidi Cao ◽  
Xiaohua Liu ◽  
Xiaoming Feng
Keyword(s):  
Conjugate Addition ◽  
Quinone Methides

scholarly journals Cover Feature: para -Quinone Methides as Acceptors in 1,6-Nucleophilic Conjugate Addition Reactions for the Synthesis of Structurally Diverse Molecules (Eur. J. Org. Chem. 18/2020)

2020 ◽  
Vol 2020 (18) ◽  
pp. 2642-2642
Author(s):  
Carolina G. S. Lima ◽  
Fernanda P. Pauli ◽  
Dora C. S. Costa ◽  
Acácio S. de Souza ◽  
Luana S. M. Forezi ◽  
...  
Keyword(s):  
Conjugate Addition ◽  
Addition Reactions ◽  
Quinone Methides

Non-hydrogen bond catalyst-mediated diastereoselective conjugate additions of 5H-oxazol-4-ones to o-hydroxyphenyl-substituted p-quinone methides

2020 ◽  
Vol 18 (35) ◽  
pp. 6807-6811
Author(s):  
Ziyang Wang ◽  
Anqi Huang ◽  
Fang Fang ◽  
Pengfei Li ◽  
Guokai Liu ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Conjugate Addition ◽  
Quinone Methides ◽  
Conjugate Additions ◽  
High Yields

An efficient DBU-catalyzed conjugate addition of 5H-oxazol-4-ones to o-hydroxyphenyl-substituted p-quinone methides has been developed, affording the valuable diarylmethanes in high yields with excellent diastereoselectivity.

1,6-Conjugate addition initiated formal [4+2] annulation of p-quinone methides with sulfonyl allenols: a unique access to spiro[5.5]undeca-1,4-dien-3-one scaffolds

2020 ◽  
Vol 56 (37) ◽  
pp. 5022-5025 ◽  
Author(s):  
Ganesh S. Ghotekar ◽  
Sachin R. Shirsath ◽  
Aslam C. Shaikh ◽  
M. Muthukrishnan
Keyword(s):  
Conjugate Addition ◽  
Quinone Methides ◽  
One Pot ◽  
One Pot Synthesis

An expedient one-pot synthesis of carbocyclic spiro[5.5]undeca-1,4-dien-3-ones via 1,6-conjugate addition initiated formal [4+2] annulation sequences by employing p-quinone methides and sulfonyl allenols.

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