2-(1-Pentyl)-1,3,2-benzodioxaborol | 32999-12-5

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 2-(1-Pentyl)-1,3,2-benzodioxaborol
• 英文别名: 2-pentyl-benzo[1,3,2]dioxaborole；2-Pentyl-1,3,2-benzodioxaborole；2-pentyl-1,3,2-benzodioxaborole
• CAS: 32999-12-5
• 化学式: C₁₁H₁₅BO₂
• 分子量: 190.05
• InChiKey: OUDOLXHURMLGJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  戊烯 、 儿萘酚硼烷 生成 2-(1-Pentyl)-1,3,2-benzodioxaborol
  参考文献：
  名称：

  1,3,2-Benzodioxaborole, a convenient monofunctional hydroborating agent. Simple new synthesis of alkaneboronic esters and acids from olefins via hydroboration

  摘要：

  DOI：

  10.1021/ja00736a061

文献信息

• Copper-Mediated Dehydrogenative C(sp³)–H Borylation of Alkanes
  作者：Ruocheng Sang、Wangyujing Han、Hanwen Zhang、Carla M. Saunders、Adam Noble、Varinder K. Aggarwal

  DOI：10.1021/jacs.3c02185

  日期：2023.7.19

  Borylations of inert carbon–hydrogen bonds are highly useful for transforming feedstock chemicals into versatile organoboron reagents. Catalysis of these reactions has historically relied on precious-metal complexes, which promote dehydrogenative borylations with diboron reagents under oxidant-free conditions. Recently, photoinduced radical-mediated borylations involving hydrogen atom transfer pathways

  惰性碳氢键的硼化对于将原料化学品转化为多功能有机硼试剂非常有用。这些反应的催化历来依赖于贵金属络合物，其在无氧化剂条件下促进二硼试剂的脱氢硼化反应。最近，涉及氢原子转移途径的光诱导自由基介导的硼基化已成为有吸引力的替代方案，因为它们提供了互补的区域选择性并在无金属条件下进行。然而，这些净氧化过程需要化学计量的氧化剂，因此无法与贵金属催化的对应物的高原子经济性竞争。在此，我们报道了 CuCl 2在无氧化剂条件下催化烷烃与双儿茶酚二硼的自由基介导的脱氢 C(sp 3 )–H 硼化反应。这是铜催化剂意想不到的双重作用的结果，它促进二硼试剂的氧化，生成亲电子的双硼酸化物，在随后的氧化还原中性光催化C-H硼化反应中充当有效的硼化剂。
• Iron-Catalyzed C(Sp³)–H Borylation, Thiolation, and Sulfinylation Enabled by Photoinduced Ligand-to-Metal Charge Transfer
  作者：Jia-Lin Tu、Ao-Men Hu、Lin Guo、Wujiong Xia

  DOI：10.1021/jacs.3c01082

  日期：——

  (LMCT) process. These reactions exhibit remarkably broad substrate scope (>150 examples in total), and most importantly, all of these three reactions show unconventional regioselectivity, with the occurrence of C(sp3)–H borylation, thiolation, and sulfinylation preferentially at the distal methyl position. The procedures are operationally simple and readily scalable and provide access to high-value products

  催化 C(sp 3 )–H 功能化为构建有机分子提供了巨大机会，促进了复杂药物化合物的衍生化。在此框架内，直接氢原子转移 (HAT) 光催化成为实现这一目标的一种有吸引力的方法。然而，这些方案中使用的可行底物是有限的，并且位点选择性显示出对活化和热力学有利的 C(sp 3 )–H 键的偏好。在此，我们描述了无向铁催化 C(sp 3)–H 硼酸化、硫醇化和亚磺酰化反应由光诱导配体到金属电荷转移 (LMCT) 过程实现。这些反应表现出非常广泛的底物范围（总共 > 150 个例子），最重要的是，所有这三个反应都表现出非常规的区域选择性，C(sp 3 )–H 硼酸化、硫醇化和亚磺酰化优先发生在远端甲基位置。这些程序操作简单，易于扩展，一步即可从简单的碳氢化合物中获取高价值产品。机理研究和对照实验表明，所提供的位点选择性不仅与 HAT 物种相关，而且在很大程度上受到硼基和砜基自由基受体的使用的影响。
• Hydroboration. XXXIX. 1,3,2-Benzodioxaborole (catecholborane) as a new hydroboration reagent for alkenes and alkynes. General synthesis of alkane- and alkeneboronic acids and esters via hydroboration. Directive effects in the hydroboration of alkenes and alkynes with catecholborane
  作者：Herbert C. Brown、S. K. Gupta

  DOI：10.1021/ja00851a038

  日期：1975.9
• Isolation of [Ru(IPr)₂(CO)H]⁺ (IPr = 1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene) and Reactivity toward E–H (E = H, B) Bonds
  作者：Ian M. Riddlestone、David McKay、Matthias J. Gutmann、Stuart A. Macgregor、Mary F. Mahon、Hazel A. Sparkes、Michael K. Whittlesey

  DOI：10.1021/acs.organomet.6b00173

  日期：2016.5.9

  Halide abstraction from the ruthenium N-heterocyclic carbene complex Ru(IPr)(2)(CO)HCl (IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) with NaBAr4F (BAr4F = BC6H3(3,5-CF3)(2)}(4)) gave the salt [Ru(IPr)(2)(CO)H]BAr4F (2), which was shown through a combined X-ray/neutron structure refinement and quantum theory of atoms in molecules (QTAIM) study to contain a bifurcated Ru center dot center dot center dot eta(3)-H2C xi-agostic interaction involving one Pr-i substituent of the IPr ligand. This system complements the previously reported [Ru(IMes)(2)(CO)H](+) cation (IMes=1,3-bis(2,4,6-trimethylphenyl)-imidazol-2-ylidene), where a non-agostic form is favored. Treatment of 2 with CO, H-2, and the amine-boranes H3B center dot NR2H (R = Me, H) gave [Ru(IPr)(2)(CO)(3)H]BAr4F (3), [Ru(IPr)(2)(CO)(eta(2)-H-2)H]BAr4F (4), and [Ru(IPr)(2)(CO)(kappa(2)-H2BH center dot NR2H)H]BAr4F (R = Me, 5; R = H, 6), respectively. Heating 5 in the presence of Me3SiCH=CH2 led to alkene hydroboration and formation of the C-H activated product [Ru(IPr)(IPr)'(CO)]BAr4F (7). X-ray characterization of 3 and 5-7 was complemented by DFT calculations, and the mechanism of H-2/H exchange in 4 was also elucidated. Treatment of 2 with HBcat resulted in Ru-H abstraction to form the boryl complex [Ru(IPr)(2)(CO)(Bcat)] BAr4F (8), which proved to be competent in the catalytic hydroboration of 1-hexene. In 8, a combined X-ray/neutron structure refinement and QTAIM analysis suggested the presence of a single Ru center dot center dot center dot eta(2)-HC xi-agostic interaction.