Article
Chemistry, Organic
Jia Seo, Che-Wei Chen, Woohyeong Lee, Ju Eun Jeon, Pei-Ling Chen, Shih-Ching Chuang, Jung Min Joo
Summary: A benzannulation strategy was developed involving activation of two C-H bonds of five-membered heteroarenes, resulting in fluorescent benzofuran and indole derivatives through Pd-catalyzed oxidative reactions. This strategy provides a potential pathway for further development of functionalized polycyclic heteroaromatic compounds.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Multidisciplinary
Shangfeng Ren, Keke Huang, Jin-Biao Liu, Lianpeng Zhang, Min Hou, Guanyinsheng Qiu
Summary: A palladium-catalyzed formal [2 + 2 + 1] cyclization of 1-alkynyl-8-iodonaphthalene with double isocyanides is developed, resulting in a series of 7H-acenaphtho[1,2-b]pyrrole compounds.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Multidisciplinary
Wang Yao, Chuan-Jun Lu, Li-Wen Zhan, Yi Wu, Jia Feng, Ren-Rong Liu
Summary: In this study, a palladium-catalyzed enantioselective C-H activation method for pyrroles was reported, which successfully synthesized structurally diverse indole-pyrrole atropisomers with a chiral N-N axis, showing high yields and enantioselectivities. Furthermore, the kinetic resolution of trisubstituted N-N heterobiaryls with more sterically demanding substituents was also achieved. This versatile method enables the rapid and selective functionalization of pyrroles, facilitating the synthesis of valuable and complex N-N atropisomers.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Guilherme Leonel, Isabella Klann, Davi F. Back, Bernardo A. Iglesias, Cristina W. Nogueira, Gilson Zeni
Summary: A method for the synthesis of 4-organoselanyl oxazinoindolone derivatives using iron(III) chloride and diorganyl diselenides as promoters has been developed. The reaction conditions tolerate a variety of diorganyl diselenides with different substituents. The reaction mechanism seems to proceed through an ionic pathway, and the cooperative action of iron(III) chloride and diorganyl diselenides is crucial for successful cyclization. Additionally, changing the electrophilic source resulted in the formation of 4-iodo-oxazinoindolones.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Peng Zhang, Qi Xu, Xiao-Mei Wang, Jia Feng, Chuan-Jun Lu, Yingzi Li, Ren-Rong Liu
Summary: The first enantioselective synthesis of N-N bisindole atropisomers via palladium-catalyzed construction of one indole skeleton is reported in this study. A wide variety of N-N axially chiral bisindoles were generated with good yields and excellent enantioselectivities through a cascade condensation/N-arylation reaction. The reaction mechanism and enantiocontrol were further investigated using density functional theory (DFT) calculations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Yoon Sung Cho, Seung Tae Kim, Do Hyun Ryu
Summary: A chiral Lewis acid-catalyzed enantioselective Friedel-Crafts alkylation using in situ-generated o-quinone methides has been developed. The reaction showed high yield (up to 99%) and excellent enantioselectivity (up to >99% ee) in the presence of a chiral oxazaborolidinium ion catalyst.
Article
Chemistry, Organic
Stephane Golling, Pierre Hansjacob, Nassim Bami, Frederic R. Leroux, Morgan Donnard
Summary: This paper reports a palladium-catalyzed annulation reaction that can synthesize polysubstituted amino-indenones, with different regioselectivity observed between different ynamides.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Sho Amemiya, Yui Takahashi, Akira Tsubouchi, Akio Saito
Summary: By controlling the conditions, 3-acylpyrrolidines can be synthesized and further subjected to a domino reaction to afford the desired product 4-alkylidene-3,4-dihydro-2H-pyrroles.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
James E. Baumann, Gojko Lalic
Summary: A new method for the differential dihydrofunctionalization of terminal alkynes has been developed, enabling the synthesis of allylic boronate esters through a reductive three-component coupling reaction. This transformation, promoted by a copper/palladium catalyst system, hydrofunctionalizes both pi-bonds of the alkyne. The method is compatible with a wide range of functional groups.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Wei Tian, Bowen Li, Duanshuai Tian, Wenjun Tang
Summary: A palladium-catalyzed 2-alkylation of indoles with alpha-bromo esters using a P,P=O ligand has been developed. The method shows excellent regioselectivities, mild reaction conditions, and good functional group compatibility. Mechanistic studies indicate that the reaction proceeds through a radical pathway.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Organic
Milos Petkovic, Milos Jovanovic, Predrag Jovanovic, Milena Simic, Gordana Tasic, Vladimir Savic
Summary: Pyrrole derivatives with C(2)-aryl substituents are an important and widespread class of heterocyclic compounds. A novel approach combining the dual role of arylating agent as nitrogen protecting group and involved in the arylation step has been developed for the direct arylation synthesis of C(2)-arylpyrroles. The deprotection as a final stage is carried out simultaneously utilizing amines as reacting components, leading to mild conditions and exclusive C(2) selectivity.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Multidisciplinary
Li-Wen Zhan, Chuan-Jun Lu, Jia Feng, Ren-Rong Liu
Summary: This study reports for the first time that palladium compounds can catalyze the hydroarylation of 1-alkynylindoles with organoborons, resulting in the synthesis of chiral C-N atropisomers. The reaction conditions are mild and lead to excellent regio-, stereo- (Z-selectivity), and enantioselectivity. The simplicity, high stereoselectivity, and good functional group tolerance of this catalytic system make it highly attractive.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Xiaolei Ji, Chaoren Shen, Xinxin Tian, Hongru Zhang, Xinyi Ren, Kaiwu Dong
Summary: In this study, a Pd-catalyzed asymmetric double hydroxycarbonylation of terminal alkynes was developed using relay catalysis, which provided an efficient route to chiral succinic acids. This method demonstrated high yields and enantioselectivity for 41 examples and showcased its synthetic utilities in the facile synthesis of key intermediates for chiral pharmaceuticals.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Nilay Kanova, Buse Aysen Dundar, Yilmaz Kelgokmen, Metin Zora
Summary: A one pot two step protocol has been developed for the synthesis of 2-acetyl-1H-pyrroles from N-propargylic beta-enaminones. The method is general, providing a diverse range of products with good to high yields and tolerating various functional groups. This operationally easy method offers a rapid access to functionalized 2-acetyl-1H-pyrroles with potential pharmacological interest.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Manjunath S. Lokolkar, Pravin A. Mane, Sandip Dey, Bhalchandra M. Bhanage
Summary: An effective method for synthesizing 2-substituted indoles through addition/reductive cyclization in a one-pot tandem reaction has been presented. This method tolerates a wide range of functional groups and provides moderate to good yields. The gram-scale synthesis of 2-substituted indole has also been demonstrated. This protocol offers an alternative route for the synthesis of 2-substituted indoles.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
