Chemical Research in Chinese Universities, Journal Year: 2022, Volume and Issue: 39(6), P. 933 - 947
Published: Nov. 21, 2022
Language: Английский
ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 3700 - 3710
Published: Feb. 14, 2025
Language: Английский
Citations
1
Organic Letters, Journal Year: 2022, Volume and Issue: 24(10), P. 1941 - 1946
Published: March 9, 2022
The development of a rational strategy for achieving site-selective C4–H halogenation indoles is an appealing yet challenging task. Herein, we disclose Pd(II)-catalyzed transient directing group (TDG)-assisted methodology realizing C4 chlorination/bromination employing glycine as the TDG and NFSI bystanding oxidant. use inexpensive commercially available CuX2 halide source key highlight this protocol. Furthermore, was also extended to accessing acetoxylated acetic acid acetate 1-fluoro-2,4,6-trimethylpyridinium triflate
Language: Английский
Citations
21
The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown
Published: Jan. 10, 2025
Pd-catalyzed C4-selective alkynylation of indoles was established by employing glycine as a transient directing group. This reaction exhibits high regioselectivity with the tolerance wide scope functional groups to afford diverse alkynylated in moderate good yields. Moreover, readily accessible scale-up synthesis and further decorations achieve multifunctionalized demonstrate synthetic potential this protocol.
Language: Английский
Citations
0
Organic Letters, Journal Year: 2025, Volume and Issue: unknown
Published: April 29, 2025
We disclose herein a catalyst-free, room-temperature protocol for the highly regio- and stereoselective alkenyl C(sp2)-H chlorination of diverse enamides with commercially available, inexpensive N-chlorosuccinimide (NCS) as electrophilic chlorinating reagent under exceedingly mild conditions. This operationally simple approach features remarkably broad substrate scope accommodates excellent functional group tolerance, affording range synthetically valuable geometrically defined β-chlorinated in high yields an exclusive E configuration.
Language: Английский
Citations
0
The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 88(3), P. 1299 - 1318
Published: May 24, 2022
Pd(II)-catalyzed C-H arylations of free (NH) indoles including different carbonyl directing groups on C3-position with aryl iodides are demonstrated. Importantly, the reactions carried out using same catalyst system without any additional transient group (TDG). In this study, formyl as a gave C4-arylated versus C2-arylation. Using system, functionalization 3-acetylindoles provided domino C4-arylation/3,2-carbonyl migration products. This transformation involves unusual acetyl to C2-position following C4-arylation in one pot. Meanwhile, could be simply controlled and N-protected afforded products group. Functionalization indole-3-carboxylic acid (or methyl ester) present Pd(II)-catalyst resulted decarboxylation followed by formation C2-arylated indoles. Based control experiments literature, plausible mechanisms proposed. The synthetic utilities these acetylindole derivatives have also been Remarkably, acetylindoles allowed construction functionalized pityiacitrin (a natural product).
Language: Английский
Citations
16
European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(31)
Published: July 4, 2023
Abstract In order to directly functionalize C−H bonds of complex molecules and, in particular, control the regioselectivity reaction, a wide range directing groups has been used. However, these need be installed and removed for further applications, which may limit use activation synthesis. Concerning aldehydes ketones, transient group strategy recently emerged overcome this drawback. The addition an additive, general amine, allowed situ formation real achieve activation. This review presents latest developments field over period 2020–2023.
Language: Английский
Citations
9
The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(9), P. 6108 - 6119
Published: April 3, 2023
An efficient and straightforward approach for the synthesis of C7 site-selective BINOL derivatives has been achieved via cost-effective Co(III)-catalyzed C-H cascade alkenylation/intramolecular Friedel-Crafts alkylation units propargyl cycloalkanols. Under advantage pyrazole directing group, protocol allows rapid various BINOL-tethered spiro[cyclobutane-1,1'-indenes].
Language: Английский
Citations
8
Organic Letters, Journal Year: 2021, Volume and Issue: 24(2), P. 554 - 558
Published: Dec. 30, 2021
Palladium-catalyzed weak chelation-assisted regioselective C4-arylation of indoles has been accomplished using a readily available arene at moderate temperature. The C4-arylation, chelating benzoyl (Bz) directing group, cross-dehydrogenative coupling (CDC), broad substrate scope, and late-stage diversifications are the important practical features.
Language: Английский
Citations
15
The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(7), P. 4254 - 4263
Published: March 10, 2023
A Pd(II)-catalyzed dehydrogenative remote C4–H coupling of indoles with unfunctionalized arenes at room temperature was reported. The weak chelating trifluoroacetyl group the C3-position served as a directing for activation. Arenes wide range substituents were employed partner in cross-coupling reaction.
Language: Английский
Citations
6
European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(24)
Published: April 24, 2023
Abstract Herein, a regioselective bromination or chlorination reaction of 1‐naphthaldehydes is described. Without additive, the palladium‐catalyzed C−H halogenation showed C8‐regioselectivity, whereas formation an aromatic imine intermediate allowed switch to C2‐reactivity. Mechanistic studies and DFT calculations were performed explain regioselectivity synthesized halogenated products used as key building blocks access polycyclic natural product skeletons.
Language: Английский
Citations
6