Double C-H functionalization in sequential order: Direct synthesis of polycyclic compounds by a palladium-catalyzed C-H alkenylation-arylation cascade

Ohno H.; Iuchi M.; Kojima N.; Yoshimitsu T.; Fujii N.; Tanaka T.

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Double C-H functionalization in sequential order: Direct synthesis of polycyclic compounds by a palladium-catalyzed C-H alkenylation-arylation cascade

机译：顺序进行双重C-H官能化：通过钯催化的C-H烯基化-芳基化级联反应直接合成多环化合物

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Palladium-catalyzed cascade C-H alkenylation and arylation provides convenient access to polycyclic aromatic compounds. Treatment of 3-bromoaniline derivatives bearing a bromocinnamyl group on the nitrogen atom with a catalytic amount of [Pd(OAc) _2] and PCy _3aHBF _4 in the presence of Cs _2CO _3 in dioxane affords naphthalene-fused indole derivatives in good yields. This double cyclization reaction is also applicable to heterocyclic substrates, giving fused indoles containing a heteroaromatic ring such as dibenzofuran, dibenzothiophene, carbazole, indole, or benzofuran through heterocyclic C-H arylation. When using a 2,6-unsubstituted aniline derivative, the first C-H arylation preferentially proceeds at the more hindered position of the aniline ring.

机译：钯催化的级联C-H链烯基化和芳基化可方便地获得多环芳族化合物。在二恶烷中存在Cs _2CO _3的情况下，用催化量的[Pd（OAc）_2]和PCy _3aHBF _4处理氮原子上带有溴肉桂基的3-溴苯胺衍生物，可以得到高产率的萘并吲哚衍生物。该双环化反应也适用于杂环底物，其通过杂环C-H芳基化得到含有杂芳族环的稠合吲哚，例如二苯并呋喃，二苯并噻吩，咔唑，吲哚或苯并呋喃。当使用2，6-未取代的苯胺衍生物时，第一C-H芳基化优先在苯胺环的受阻位置进行。

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《Chemistry: A European journal》 |2012年第17期|共9页
作者
Ohno H.; Iuchi M.; Kojima N.; Yoshimitsu T.; Fujii N.; Tanaka T.;
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正文语种 eng
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C-H bond activation; domino reactions; heterocycles; palladium; polycycles;

机译：C-H键活化;多米诺反应;杂环;钯;多环;

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1. Double C-H functionalization in sequential order: Direct synthesis of polycyclic compounds by a palladium-catalyzed C-H alkenylation-arylation cascade [J] . Ohno H., Iuchi M., Kojima N., Chemistry: A European journal . 2012,第17期

机译：顺序进行双重C-H官能化：通过钯催化的C-H烯基化-芳基化级联反应直接合成多环化合物
2. A direct palladium-catalyzed route for the synthesis of benzo[a]carbazoles through sequential C-C bond formation and C-H bond functionalization [J] . Kianmehr E., Ghanbari M. European journal of organic chemistry . 2012,第2期

机译：通过顺序C-C键形成和C-H键官能化的直接钯催化路线合成苯并[a]咔唑
3. Palladium-catalyzed direct C-H nitration and intramolecular C-H functionalization for the synthesis of 3-nitro-1-(phenylsulfonyl)-1H-indazole derivatives [J] . Wang Guodong, Sun Jian, Wang Kai, Organic Chemistry Frontiers . 2019,第10期

机译：钯催化的直接C-H硝化和分子内C-H官能化，用于合成3硝基-1-（苯磺酰基）-1H-吲唑衍生物
4. Synthesis of Helicenes Utilizing Palladium-Catalyzed Double C-H Arylation Reaction [C] . Ken Kamikawa, Ippei Takemoto, Shin Takemoto Symposium on Organometallic Chemistry . 2007

机译：利用钯催化的双C-H芳基化反应的螺旋合成
5. STUDIES IN ORGANOSULFUR CHEMISTRY. I. NUCLEAR MAGNETIC RESONANCE (PROTON, CARBON-13, OXYGEN-17 (1) J(C-H)) INVESTIGATIONS OF ORGANOSULFUR COMPOUNDS. II. MECHANISTIC STUDY OF PHASE TRANSFER CATALYZED REACTIONS OF DICHLOROCARBENE WITH SULFIDES AND SULFOXIDES. III. STUDIES DIRECTED TOWARD ASYMMETRIC SYNTHESIS USING CHIRAL PHASE TRANSFER CATALYSTS. [D] . DYER, JOHN COLLINS. 1980

机译：有机硫化学研究。 I.有机硫化合物的核磁共振（质子，碳13，氧17（1）J（C-H））研究。二。二氯卡宾与硫化物和硫化物的相转移催化反应的机理研究。三，使用手性相转移催化剂进行不对称合成的研究。
6. Palladium-Catalyzed C-H Functionalization Using Guanidine as a Directing Group: Ortho Arylation and Olefination of Arylguanidines [O] . Jiaan Shao, Wenteng Chen, Marc A. Giulianotti, -1

机译：钯催化C-H官能使用胍作为定向基团：邻芳基化和胍类物质的烯化
7. Palladium-Catalyzed Synthesis of Cyclopentane-Fused Benzocyclobutenes via Tandem Directed Carbopalladation/C-H Bond Functionalization [O] . -1

机译：钯催化通过串联定向碳酸盐/ C-H键官能化合成环戊烷稠合苯并环丁烯
8. Direct Selective Acylation of an Unactivated C-H Bond in a Caged Hydrocarbon.Approach to Systems for C-H Bond Functionalization That Proceed Catalytically and Selectively at High Substrate Conversion [R] . Prosser-McCartha, C. M., Hill, C. L. 1990

机译：笼型烃中未活化C-H键的直接选择性酰化。用于C-H键官能化的系统，在高基质转化下催化和选择性地进行

Double C-H functionalization in sequential order: Direct synthesis of polycyclic compounds by a palladium-catalyzed C-H alkenylation-arylation cascade

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