Pyridine sulfinates as general nucleophilic coupling partners in palladium-catalyzed cross-coupling reactions with aryl halides.
Pyridine sulfinates as general nucleophilic coupling partners in palladium-catalyzed cross-coupling reactions with aryl halides.
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DOI：
10.1039/c7sc00675f
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发表时间：
2017-06-01
期刊：
影响因子：
8.4
通讯作者：
Willis MC
中科院分区：
文献类型：
--
作者：
Markovic T;Rocke BN;Blakemore DC;Mascitti V;Willis MC
Pyridine sulfinates are stable and straightforward to prepare nucleophilic coupling partners for palladium catalyzed cross-coupling reactions with aryl and heteroaryl halides. The scope with respect to the halides coupling partner is considerable, and allows the preparation of a broad range of linked pyridines. Pyridine rings are ubiquitous in drug molecules; however, the pre-eminent reaction used to form carbon–carbon bonds in the pharmaceutical industry, the Suzuki–Miyaura cross-coupling reaction, often fails when applied to these structures. This phenomenon is most pronounced in 2-substituted pyridines, and results from the difficulty in preparing, the poor stability of, and low efficiency in reactions of pyridine-2-boronates. We demonstrate that by replacing these boronates with pyridine-2-sulfinates, a cross-coupling process of unrivalled scope and utility is realized. The corresponding 3- and 4-substituted pyridine variants are also efficient coupling partners. In addition, we apply these sulfinates in a library format to the preparation of medicinally relevant derivatives of the drugs varenicline (Chantix) and mepyramine (Anthisan).
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影响因子：
16.6
作者：
Emmett, Edward J.;Hayter, Barry R.;Willis, Michael C.
通讯作者：
Willis, Michael C.
影响因子：
15
作者：
Nguyen, Bao;Emmett, Edward J.;Willis, Michael C.
通讯作者：
Willis, Michael C.
影响因子：
7.3
作者：
Brow, Dean G.;Bostrom, Jonas
通讯作者：
Bostrom, Jonas
影响因子：
7.3
作者：
Penning, TD;Talley, JJ;Isakson, PC
通讯作者：
Isakson, PC
影响因子：
1.8
作者：
MIYAURA, N;YAMADA, K;SUZUKI, A
通讯作者：
SUZUKI, A