Synthesis of Indolyl‐1,3‐dienes from β ‐Sulphonyl Aldehydes through One‐Pot Sequential Brønsted Acid/Base Catalysis DOI
Ganesh Karan, Samrat Sahu, Modhu Sudan Maji

et al.

European Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 2022(18)

Published: April 8, 2022

Abstract Introduction of a 1,3‐diene moiety at the C3‐position pyrrole and indole bearing various aliphatic as well aromatic functional groups with good stereoselectivity remains challenging task. Keeping synthetic applicability in mind, an eccentric strategy is developed to synthesize 1,3‐dienyl pyrroles indoles from unprotected employing β‐sulphonyl aldehyde dienylating agent. This method by using one‐pot sequential Brønsted acid/base catalysis strategy. The nucleophilicity transmitted through conjugation eliminate sulfonyl step‐wise manner. Further, this protocol was extended incorporation 1,3,5‐triene unprecedented successive three group elimination. As application strategy, Diels−Alder reaction hydrothiolation were demonstrated.

Language: Английский

Recent Developments of Palladium- and Rhodium-Catalyzed β-Carbon Elimination Strategies DOI
Austin D. Marchese, Bijan Mirabi, Mark Lautens

et al.

Synthesis, Journal Year: 2023, Volume and Issue: 55(15), P. 2285 - 2303

Published: Jan. 22, 2023

Abstract The activation of C–C bonds via transition metal catalysis has become an increasingly popular strategy in organic synthesis. An emerging method to cleave is facilitate a β-carbon elimination using rhodium or palladium catalysis. This elementary step typically relies on thermodynamic driving force, such as the relief ring strain steric strain. More recently, use neopentyl species chelation assistance enabled this difficult transformation. review will cover recent synthetic applications eliminations under and 1 Introduction 2 Chelation-Assisted β-Carbon Elimination Reactions 3 from Neopentyl–Pd Species 4 Pd-Catalyzed Catellani 5 Cyclopropanes 6 Conclusion

Language: Английский

Citations

10
Rh(III)-Catalyzed Dienylation and Cyclopropylation of 1,2,3-Benzotriazinones with Alkylidenecyclopropanes DOI
Yanzhi Liu, Yao‐Fu Zeng,

Jiaohang Wei

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(28), P. 5179 - 5184

Published: July 6, 2023

Rh (III)-catalyzed dienylation and cyclopropylation of 1,2,3-benzotriazinones with alkylidenecyclopropanes (ACPs) has been achieved. Different from the previous reports 1,2,3-benzotriazinones, triazinone ring remained intact in this C-H bond functionlization reaction. Also, denitrogenative could also be realized by changing reaction temperature. This protocol is featured high E selectivity, wide substrate scope, divergent structures products.

Language: Английский

Citations

7
Rh(iii)-Catalyzed dienylation and cyclopropylation of indoles at the C4 position with alkylidenecyclopropanes DOI
Yanzhi Liu, Yao‐Fu Zeng, Bing Shu

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(16), P. 4287 - 4293

Published: Jan. 1, 2022

Herein, we report a Rh( iii )-catalyzed C–H functionalization of indoles at the C4 position with alkylidenecyclopropanes (ACPs).

Language: Английский

Citations

7
Transition Metal‐Catalyzed C2 and C3 Functionalization of Indoles DOI Open Access

Pinki Sihag,

Meledath Sudhakaran Keerthana,

Masilamani Jeganmohan

et al.

Published: March 25, 2023

Transition metal-catalyzed C2 and C3 functionalization of indoles has been summarized in this article. This chapter encompasses a wide range useful directed non-directed transformations. article highlights selective with respect to C–H arylation, alkenylation, alkynylation, acylation, nitration, borylation, annulations, amidation using coupling partners.

Language: Английский

Citations

0
Synthesis of Indolyl‐1,3‐dienes from β ‐Sulphonyl Aldehydes through One‐Pot Sequential Brønsted Acid/Base Catalysis DOI
Ganesh Karan, Samrat Sahu, Modhu Sudan Maji

et al.

European Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 2022(18)

Published: April 8, 2022

Abstract Introduction of a 1,3‐diene moiety at the C3‐position pyrrole and indole bearing various aliphatic as well aromatic functional groups with good stereoselectivity remains challenging task. Keeping synthetic applicability in mind, an eccentric strategy is developed to synthesize 1,3‐dienyl pyrroles indoles from unprotected employing β‐sulphonyl aldehyde dienylating agent. This method by using one‐pot sequential Brønsted acid/base catalysis strategy. The nucleophilicity transmitted through conjugation eliminate sulfonyl step‐wise manner. Further, this protocol was extended incorporation 1,3,5‐triene unprecedented successive three group elimination. As application strategy, Diels−Alder reaction hydrothiolation were demonstrated.

Language: Английский

Citations

0