Tandem Blaise/Palladium-Catalyzed Ullmann Coupling for the One-Pot Synthesis of Enamino Ester-Functionalized Biaryls from Nitriles.
Xuan, Zi; Kim, Ju Hyun; Lee, Sang-Gi; The Journal of organic chemistry 80 (2015) 7824–7829; doi:10.1021/acs.joc.5b01375

data_4031319
_publ_section_title
;
 Tandem Blaise/Palladium-Catalyzed Ullmann Coupling for the One-Pot
 Synthesis of Enamino Ester-Functionalized Biaryls from Nitriles.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7824
_journal_page_last               7829
_journal_paper_doi               10.1021/acs.joc.5b01375
_journal_volume                  80
_journal_year                    2015
_chemical_formula_sum            'C22 H24 N2 O4.4'
_chemical_formula_weight         388.43
_chemical_name_common            ye218
_space_group_crystal_system      trigonal
_space_group_IT_number           147
_space_group_name_Hall           '-P 3'
_space_group_name_H-M_alt        'P -3'
_symmetry_space_group_name_Hall  '-P 3'
_symmetry_space_group_name_H-M   'P -3'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   15.8651(5)
_cell_length_b                   15.8651(5)
_cell_length_c                   15.0224(5)
_cell_measurement_reflns_used    2765
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      13.6834
_cell_measurement_theta_min      2.5672
_cell_volume                     3274.58(18)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2725
_diffrn_reflns_av_unetI/netI     0.1188
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            76955
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1236
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.889
_refine_diff_density_min         -0.205
_refine_ls_extinction_coef       0.016(3)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         4247
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.950
_refine_ls_R_factor_all          0.1913
_refine_ls_R_factor_gt           0.0720
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1216P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1744
_refine_ls_wR_factor_ref         0.2404
_reflns_number_gt                1729
_reflns_number_total             4247
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b01375_si_002.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 4031319--4031320.cif.'
_cod_original_cell_volume        3274.6(2)
_cod_database_code               4031319