Palladium-Catalyzed Synthesis of 3-Acylated Indoles Involving Oxidative Cross-Coupling of Indoles with α-Amino Carbonyl Compounds
Ri-Yuan Tang; Xiao-Kang Guo; Jian-Nan Xiang; Jin-Heng Li; Journal of Organic Chemistry 78 (2013) 11163–11171; doi:10.1021/jo402215s

data_4028769
_publ_section_title
;
 Palladium-Catalyzed Synthesis of 3-Acylated Indoles Involving Oxidative
 Cross-Coupling of Indoles with \a-Amino Carbonyl Compounds
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              11163
_journal_page_last               11171
_journal_paper_doi               10.1021/jo402215s
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C16 H11 N O2'
_chemical_formula_sum            'C16 H11 N O2'
_chemical_formula_weight         249.26
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                82.128(7)
_cell_angle_beta                 89.698(8)
_cell_angle_gamma                64.857(7)
_cell_formula_units_Z            2
_cell_length_a                   7.440(3)
_cell_length_b                   8.520(3)
_cell_length_c                   10.916(4)
_cell_measurement_reflns_used    1697
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.84
_cell_measurement_theta_min      2.67
_cell_volume                     619.4(4)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'XP (Bruker, 2002)'
_computing_publication_material  'SHELXL-97 (Bruker, 2002)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX II area-detector diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0473
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4847
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9868
_exptl_absorpt_correction_T_min  0.9798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       Block
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.13(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2268
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0652
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1236P)^2^+0.1571P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1912
_refine_ls_wR_factor_ref         0.2021
_reflns_number_gt                1598
_reflns_number_total             2268
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo402215s_si_002.cif
_cod_data_source_block           mo_20111227a_0m
_cod_database_code               4028769