Insertion of benzyne into the Pd-C bond. Synthesis of unnatural amino acid derivatives by sequential insertion of benzyne and CO: 2,2'-functionalized biaryls containing alkylamino and carboxymethyl substituents. Isolation of stable carbopalladated-benzyne intermediates
Jose-Antonio Garcia-Lopez; Maria-Jose Oliva-Madrid; Isabel Saura-lamas; Delia Bautista; Jose Vicente; Chem.Commun. 48 (2012) 6744–; doi:10.1039/c2cc32975a

data_7107927
_publ_section_title
;
 Insertion of benzyne into the Pd-C bond. Synthesis of unnatural amino
 acid derivatives by sequential insertion of benzyne and CO:
 2,2'-functionalized biaryls containing alkylamino and carboxymethyl
 substituents. Isolation of stable carbopalladated-benzyne intermediates
;
_journal_name_full               Chem.Commun.
_journal_page_first              6744
_journal_paper_doi               10.1039/c2cc32975a
_journal_volume                  48
_journal_year                    2012
_chemical_formula_sum            'C22 H25 Cl N2 Pd'
_chemical_formula_weight         459.29
_chemical_name_systematic
;
?
;
_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                73.850(2)
_cell_angle_beta                 78.692(2)
_cell_angle_gamma                65.084(2)
_cell_formula_units_Z            2
_cell_length_a                   9.2021(7)
_cell_length_b                   10.3321(7)
_cell_length_c                   11.8365(9)
_cell_measurement_reflns_used    8692
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.60
_cell_measurement_theta_min      2.23
_cell_volume                     976.33(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       \w-scan
_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  0.0182
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11858
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.60
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    1.095
_exptl_absorpt_correction_T_max  0.9372
_exptl_absorpt_correction_T_min  0.7988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment
'NH2 free with SADI, rigid methyls, others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4558
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0229
_refine_ls_R_factor_gt           0.0220
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0218P)^2^+0.7336P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0531
_refine_ls_wR_factor_ref         0.0536
_reflns_number_gt                4424
_reflns_number_total             4558
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc32975a.txt
_cod_data_source_block           jaj561s
_cod_original_cell_volume        976.33(12)
_cod_database_code               7107927