Synthesis of Disubstituted Dithioethers: tert-Butoxide Promoted Elimination/Ring Opening of 1,3-Dithianes Followed by PalladiumCatalyzed C-S Bond Formation

被引：15

作者：

Abidi, Nissa ^{[1
]}

Schmink, Jason R. ^{[1
]}

机构：

[1] Bryn Mawr Coll, Dept Chem, Bryn Mawr, PA 19010 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 08期

基金：

美国国家科学基金会;

关键词：

COPPER-CATALYZED SYNTHESIS; VINYL SULFIDE; ADDITION-REACTIONS; DIARYL; DITHIOACETALS; SUBSTITUENT; CYCLIZATION; ACTIVATION; INHIBITORS; ARYLATION;

D O I：

10.1021/acs.joc.5b00547

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report the tandem base-promoted elimination/ring-opening of 2-benzyl-1,3-dithianes with subsequent cross coupling of the pendent thiol with a range of aryl bromides. A simple Pd(OAc)(2)/Xantphos catalyst system affects this new reaction and is compatible with a wide range of functional groups, including heteroaromatic coupling partners. The transformation proceeds in good to excellent yields (6999%) and exhibits strong stereoselectivity, forming the E-alkene as the major diastereomer. This new methodology provides access to nonsymmetric propylene styryl/aryl dithioethers, a previously undisclosed motif.

引用

页码：4123 / 4131

页数：9

共 51 条

[1] Stereoselective azide introduction during 1,2-sulfur migration in α-hydroxyalkyldithioacetals
Afonso, CAM
Barros, MT
Maycock, CD
[J]. TETRAHEDRON, 1999, 55 (03) : 801 - 814
[2] Regioselective Michael-induced cyclisation of γ- and δ-hydroxy vinyl sulfides and vinyl dithiocarbamates
Aucagne, V
Lorin, C
Tatibouët, A
Rollin, P
[J]. TETRAHEDRON LETTERS, 2005, 46 (25) : 4349 - 4352
[3] Basha F. Z., 1993, U.S. Patent, Patent No. [5,180,733, 5180733]
[4] Carbon-Sulfur Bond Formation Catalyzed by [Pd(IPr*OMe)(cin)Cl] (cin = cinnamyl)
Bastug, Gulluzar
Nolan, Steven P.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (18) : 9303 - 9308
[5] Copper-catalyzed synthesis of vinyl sulfides
Bates, CG
Saejueng, P
Doherty, MQ
Venkataraman, D
[J]. ORGANIC LETTERS, 2004, 6 (26) : 5005 - 5008
[6] Transition-Metal-Catalyzed C-S, C-Se, and C-Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions
Beletskaya, Irina P.
Ananikov, Valentine P.
[J]. CHEMICAL REVIEWS, 2011, 111 (03) : 1596 - 1636
[7] SYNTHESIS OF SOME 1-OXA-1-DETHIACEPHALOSPORINS
BRANCH, CL
PEARSON, MJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (09): : 2268 - 2275
[8] TOTAL SYNTHESIS OF (+)-LAURENCIN - USE OF ACETAL-VINYL SULFIDE CYCLIZATIONS FOR FORMING HIGHLY FUNCTIONALIZED 8-MEMBERED CYCLIC ETHERS
BRATZ, M
BULLOCK, WH
OVERMAN, LE
TAKEMOTO, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (22) : 5958 - 5966
[9] Catalytic carbon-sulfur bond formation by amphoteric vanadyl triflate: exploring with thia-Michael addition, thioacetalization, and transthioacetalization reactions
Chen, Chien-Tien
Lin, Yow-Dzer
Liu, Cheng-Yuan
[J]. TETRAHEDRON, 2009, 65 (50) : 10470 - 10476
[10] Synthesis of Aryl Thioethers through the N-Chlorosuccinimide-Promoted Cross-Coupling Reaction of Thiols with Grignard Reagents
Cheng, Jun-Hao
Ramesh, Chintakunta
Kao, Hsin-Lun
Wang, Yu-Jen
Chan, Chien-Ching
Lee, Chin-Fa
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (22) : 10369 - 10374

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