Mutualism in organic synthetic chemistry: Simultaneous heterodehydrocoupling of hydrostannane and reduction of quinoline

doi:10.1016/S1872-2067(23)64590-5

Abstract

Abstract:

Here we report a one-pot strategy to simultaneously achieve both the heterodehydrocoupling of hydrostannane and reduction of quinoline by using B(C₆F₅)₃ as catalyst under mild conditions. This method realizes the synthesis of heteroatom-tin complexes (NSn/OSn/PSn/SSn) by the same catalyst system. With the assistance of quinoline, the substrate scope was broadened and ESn yield was significantly enhanced. During the reaction, the generated heterodehydrocoupling intermediate [ESnH]⁺[HB(C₆F₅)₃]^- would accelerate the quinoline reduction by transforming 1,4-N-stannyl-dihydroquinoline intermediate into N-stannyl-tetrahydroquinoline whereas 1,4-N-stannyl-dihydroquinoline could serve as hydrogen acceptor to facilitate the conversion of [ESnH]⁺[HB(C₆F₅)₃]^- intermediate to produce ESn (E = N/O/P/S). The metathetical reaction of N-stannyl-tetrahydroquinoline and EH rapidly generates ESn and tetrahydroquinolines, thus mutually promoting the above process. The reaction mechanism is proposed on the basis of control experiments, capture and synthesis of key intermediates and deuterium experiments.

Key words: Mutualism, B(C₆F₅)₃, Heterodehydrocoupling, Reduction reaction, Quinoline

Tianwei Liu, Jianghua He, Yuetao Zhang. Mutualism in organic synthetic chemistry: Simultaneous heterodehydrocoupling of hydrostannane and reduction of quinoline[J]. Chinese Journal of Catalysis, 2024, 58: 129-137.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(23)64590-5

https://www.cjcatal.com/EN/Y2024/V58/I3/129

Figures/Tables 9

Scheme 1. (a) Traditional ESn synthesis. (b) Frustrated Lewis Pair (FLP) catalyzed reduction of N-Heterocycles by H2. (c) Mutual promotion between borylation/silylation of indoles and reduction of quinolines (our previous work, ref. 39). (d) B(C6F5)3 catalyzed ESn (E = S, O, N, P) bond formation assisted by quinoline (this work).

Table 1 Scope for the B(C6F5)3 catalyzed dehydrocoupling of (nBu)3SnH and EH (E = S) a.

Table 2 Scope for the B(C6F5)3-catalyzed dehydrocoupling of (nBu)3SnH and EH (E = O/N/P).

Table 3 Scope of EH (E= S/O/N/P) for reaction with quinolone.

Table 4 Scope of quinolines for the mutual promotion reaction.

Entry	R	Yield (%)		Entry	R	Yield (%)
Entry	R	6g	13	Entry	R	6g	13
1	R = 2-Me	92	13b 92	10	R = 6-F	97	13k 97
2	R = 3-Me	83	13c 83	11	R = 6-Cl	96	13l 96
3	R = 4-Me	29	13d 0	12	R = 6-Br	95	13m 95
4	R = 5-Me	90	13e 90	13	R = 7-Br	97	13n 95
5	R = 6-Me	98	13f 98	14	R = 8-Br	96	13o 95
6	R = 6-OMe	92	13g 92	15	R = 6-Br, 7-F	95	13p 95
7	R = 7-Me	93	13h 93	16	R=6-Br, 5,7-F	89	13q 89
8	R = 8-Me	97	13i 97	17	R = 2-Ph	91	13r 91
9	R = 5-Br	97	13j 97

Scheme 2. Control experiments.

Fig. 1. Reaction process monitoring of the B(C6F5)3-catalyzed reaction of 2e with quinoline and (nBu)3SnH at RT.

Scheme 3. Possible mechanism for the quinoline assisted ESn bond formation catalyzed by B(C6F5)3.

Scheme 4. Deuterium-labelled experiments.

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